4-(3′,4′-heterocyclyl benzoyl) pyrazoles as herbicidal agents

ABSTRACT

The invention relates to pyrazolyl derivatives of benzo-condensated, unsaturated 5-membered nitrogen heterocycles of the general formula (I), wherein X represents N or a group C—R 3 ; Y is O, S, SO, SO 2  or NR 4  or X—Y is S═N, and wherein X means sulfur, and the variables R 1 , R 2  and Pz have the meanings indicated in claim  1 . The invention, further relates to a method of producing said compounds, to agents that contain them and to their use as herbicidal agents.

This is a 371 of International application PCT/EP00/04040 filed May 5, 2000. The present invention relates to pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles, to processes for preparing such pyrazolyl derivatives, to compositions comprising such compounds, and to the use of the pyrazoyl derivatives or of the compositions comprising them for controlling harmful plants.

WO 96/05197 discloses saccharin derivatives having herbicidal action which are substituted on the benzene ring of the saccharin skeleton by a (5-hydroxypyrazol-4-yl)carbonyl radical. WO 97/30993 and WO 97/09327 disclose dioxothiochromane derivatives and dihydrobenzothiophene derivatives having herbicidal action which likewise have a (5-hydroxypyrazol-4-yl)carbonyl radical on the benzene ring of the sulfur heterocycles.

WO 97/08164 discloses, inter alia, benzo-fused derivatives of γ-butyrolactam having herbicidal action which likewise have a (5-hydroxypyrazol-4-yl)carbonyl radical.

However, the herbicidal properties of the compounds known from the publications mentioned and their compatibility with crop plants do not meet all of the criteria required from herbicides.

EP-A-822 187 discloses herbicides based on aryl-substituted pyrazoles of the formula

where R¹ is hydrogen or a protective group suitable for a pesticide, R⁴ is preferably hydrogen and R² and R³ are phenyl, naphthyl or heterocyclic groups which are unsubstituted or substituted. R³ is preferably a 5- or 6-membered heterocyclic ring and in particular a thiophene group. The herbicidal action of the compounds described in this publication and their crop plant compatibility are likewise not satisfactory.

It is an object of the present invention to provide novel compounds having herbicidal action which preferably have greater activity than the herbicidal substances of the prior art and/or better selectivity with respect to harmful plants.

We have found that this object is achieved by pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formula I defined below.

Consequently, the present invention relates to pyrazolyl derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formla I,

where

X is N or a group C—R³;

Y is O, S, SO, SO₂ or NR⁴; or

X—Y is S═N, and X is sulfur;

R¹ is hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, or di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl;

R² is hydrogen, halogen or C₁-C₆-alkyl;

R³ is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto, thiocyanato, hydrazide, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-aminoalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-hydroxyalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,

is C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of C₁-C₄-alkoxy and hydroxyl,

is C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-hydroxyalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,

is phenyl, naphthyl, heterocyclyl, phenylamino, phenoxy, diphenylamino, where the phenyl and heterocyclyl groups of the six last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,

is C(O)OR⁵, or C(O)N(R⁶)R⁷;

R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,

is phenyl, naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; where

R⁵ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,

is phenyl, naphthyl or heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and

R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,

are phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

and Pz is a radical of the formula IIa or IIb,

 where the variables R⁸, R⁹ and R¹⁰ are as defined below:

R⁸ is hydroxyl, mercapto, halogen, OR¹¹, SR¹¹, SOR¹², SO₂R¹², OSO₂R¹², P(O)R¹³R¹⁴, OP(O)R¹³R¹⁴, P(S)R¹³R¹⁴, OP(S)R¹³R¹⁴, NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R¹⁰ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio;

R¹¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, di(C₁-C₆-alkyl)aminothiocarbonyl or C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)—N-(phenyl)aminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterdcyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)—N-(heterocyclyl)aminocarbonyl, or heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹² is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl;

is phenyl, phenyl-C₁-C₆-alkyl, heterocyclyl or heterocyclyl-C₁-C₆-alkyl, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹³, R¹⁴ independently of one another are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁵ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three radicals selected from the following group: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; and

R¹⁶ is hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, C₃-C₆-alkynyl;

and their agriculturally useful salts.

Furthermore we have found herbicidal compositions which comprise the pyrazolyl derivatives of the formula I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the pyrazolyl derivatives of the formula I.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or diasteromer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. In general, the salts of those cations and the acid addition salts of those acids are suitable whose cations and anions, respectively, do not negatively affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

For R⁸=hydroxyl or mercapto {Z=O,S}, IIa also represents the tautomeric forms IIa′ and IIa″

and IIb also represents the tautomeric forms IIb′ and IIb″

The organic molecular moieties mentioned for the substituents R¹ to R¹⁶ or as radicals on phenyl and heterocyclyl radicals are collective terms for individual enumerations of the particular group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N,N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N-alkylcarbonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, alkoxyiminoalkyl, phenylalkylcarbonyl, heterocyclylalkylcarbonyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl or alkynediyl moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The expression halogen represents in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)amino, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, (C₃-C₆-alkynyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkyl)—N-phenylaminocarbonyl, N—(C₁-C₆-alkyl)—N-heterocyclylaminocarbonyl: C₁-C₄-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

C₁-C₆-haloalkyl, and the haloalkyl moieties of N—C₁-C₆-haloalkylamino: C₁-C₄-haloalkyl, as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;

C₁-C₆-alkoxy, and the alkoxy moieties of N—C₁-C₆-alkoxyamino, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)amino, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy) aminocarbonyl and N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkoxy)aminocarbonyl: C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;

C₁-C₄-alkylthio (C₁-C₄-alkylsulfanyl: C₁-C₄-alkyl-S—): for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;

C₁-C₆-alkylthio, and the alkylthio moieties of C₁-C₆-alkylthiocarbonyl: C₁-C₄-alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio as mentioned above, and also 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;

C₁-C₄-alkylsulfinyl (C₁-C₄-alkyl-S(═O)—): for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;

C₁-C₆-alkylsulfinyl: C₁-C₄-alkylsulfinyl as mentioned above, and also pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁-C₄-haloalkylsulfinyl: a C₁-C₄-alkylsulfinyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;

C₁-C₆-haloalkylsulfinyl: C₁-C₄-haloalkylsulfinyl as mentioned above, and also 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl: C₁-C₄-alkylsulfonyl, as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;

C₁-C₆-haloalkylsulfonyl: C₁-C₄-haloalkylsulfonyl as mentioned above, and also 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;

C₁-C₆-alkylamino: methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;

di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

di(C₁-C₆-alkyl)amino: di(C₁-C₄-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;

C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;

C₁-C₆-alkylcarbonyl, and the alkylcarbonyl radicals of C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonylamino: C₁-C₄-alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;

C₁-C₄-haloalkylcarbonyl: a C₁-C₄-alkylcarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-diflubropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;

C₁-C₆-haloalkylcarbonyl: a C₁-C₄-haloalkylcarbonyl radical as mentioned above, and also 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;

C₁-C₄-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;

C₁-C₆-alkoxycarbonyl: C₁-C₄-alkoxydarbonyl as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl;

C₁-C₄-haloalkoxycarbonyl: a C₁-C₄-alkoxycarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbnyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;

C₁-C₆-halooxycarbonyl: a C₁-C₄-halooxycarbonyl radical as mentioned above, and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;

(C₁-C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;

(C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;

(C₁-C₆-alkylamino)carbonyl: (C₁-C₄-alkylamino)carbonyl as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;

di(C₁-C₄-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;

di(C₁-C₆-alkyl)aminocarbonyl: di(C₁-C₄-alkyl)aminocarbonyl as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-(2-methylbutyl)aminocarbonyl, N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl, N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methylpentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1-ethylbutyl)aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;

di(C₁-C₆-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl, N,N-di(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di(1-methylpropyl)aminothiocarbonyl, N,N-di(2-methylpropyl)aminothiocarbonyl, N,N-di(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl, N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N-(1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(2-methyl-propyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylaminothiocarbonyl, N-(2-methylpropyl)-N-propylaminothiocarbonyl, N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-(1-methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methylpropyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1-methylbutyl)amino-thiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-methylpentyl)aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyl, N-methyl-N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothiocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothiocarbonyl, N-Ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methylpentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethyl-butyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;

C₁-C₆-hydroxyalkyl: C₁-C₆-alkyl which is substituted by one to three OH groups, for example hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-bishydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 2,2-dimethyl-3-hydroxypropyl;

phenyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by a phenyl radical, for example benzyl, 1-phenylethyl and 2-phenylethyl, where the phenyl radical may, in the manner mentioned, be partially or fully halogenated or may carry one to three of the substituents mentioned above for phenyl; correspondingly, heterocyclyl-C₁-C₆-alkyl is a C₁-C₆-alkyl which is substituted by a heterocyclyl radical;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl;

C₁-C₆-alkoxy-C₁-C₆-alkoxy, and the alkoxyalkoxy moieties of C₁-C₆-alkoxy-C₁-C₆-alkoxycarbonyl: C₁-C₆-alkoxy which is substituted by C₁-C₆-alkoxy as mentioned above, i.e, for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;

C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by a C₁-C₆-alkylcarbonyl group, where both of the C₁-C₆-alkyl groups may carry one or more substituents selected from C₁-C₄-alkoxy and/or hydroxyl: for example acetylmethyl (=2-oxopropyl), 2-(acetyl)ethyl (=3-oxo-n-butyl), 3-oxo-n-pentyl, 1,1-dimethyl-2-oxopropyl, 3-hydroxy-2-oxopropyl or 3-hydroxy-2-oxobutyl;

C₃-C₆-alkenyl, and the alkenyl moieties of C₃-C₆-alkenylcarbonyl, C₃-C₆-alkenyloxy, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkenylaminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy)aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl, and the alkenyl moieties of C₂-C₆-alkenylcarbonyl, phenyl-C₂-C₆-alkenylcarbonyl and heterocyclyl-C₂-C₆-alkenylcarbonyl: C₃-C₆-alkenyl as mentioned above, and also ethenyl;

C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;

C₃-C₆-alkynyl, and the alkynyl moieties of C₃-C₆-alkynylcarbonyl, C₃-C₆-alkynyloxy, C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkoxy)aminocarbonyl: for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;

C₂-C₆-alkynyl, and the alkynyl moieties of C₂-C₆-alkynylcarbonyl: C₃-C₆-alkynyl as mentioned above, and also ethynyl;

C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

C₁-C₆-alkanediyl: methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl, 1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3-diyl, pentane-2,2-diyl, 1-methylbutane-1,1-diyl, 1-methylbutane-1,2-diyl, 1-methylbutane-1,3-diyl, 1-methylbutane-1,4-diyl, 2-methylbutane-1,1-diyl, 2-methylbutane-1,2-diyl, 2-methylbutane-1,3-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylpropane-1,1-diyl, 2,2-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,2-diyl, 2,3-dimethylpropane-1,3-diyl, 2,3-dimethylpropane-1,2-diyl, 1,3-dimethylpropane-1,3-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-1,3-diyl, hexane-1,4-diyl, hexane-1,5-diyl, hexane-1,6-diyl, hexane-2,5-diyl, 2-methylpentane-1,1-diyl, 1-methylpentane-1,2-diyl, 1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl, 1-methylpentane-1,5-diyl, 2-methylpentane-1,1-diyl, 2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl, 2-methylpentane-1,4-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl, 3-methylpentane-1,3-diyl, 3-methylpentane-1,4-diyl, 3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl, 1,1-dimethylbutane-1,3-diyl, 1,1-dimethylbutane-1,4-diyl, 1,2-dimethylbutane-1,1-diyl, 1,2-dimethylbutane-1,2-diyl, 1,2-dimethylbutane-1,3-diyl, 1,2-dimethylbutane-1,4-diyl, 1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl, 1,3-dimethylbutane-1,3-diyl, 1,3-dimethylbutane-1,4-diyl, 1-ethylbutane-1,1-diyl, 1-ethylbutane-1,2-diyl, 1-ethylbutane-1,3-diyl, 1-ethylbutane-1,4-diyl, 2-ethylbutane-1,1-diyl, 2-ethylbutane-1,2-diyl, 2-ethylbutane-1,3-diyl, 2-ethylbutane-1,4-diyl, 2-ethylbutane-2,3-diyl, 2,2-dimethylbutane-1,1-diyl, 2,2-dimethylbutane-1,3-diyl, 2,2-dimethylbutane-1,4-diyl, 1-isopropylpropane-1,1-diyl, 1-isopropylpropane-1,2-diyl, 1-isopropylpropane-1,3-diyl, 2-isopropylpropane-1,1-diyl, 2-isopropylpropane-1,2-diyl, 2-isopropylpropane-1,3-diyl, 1,2,3-trimethylpropane-1,1-diyl, 1,2,3-trimethylpropane-1,2-diyl or 1,2,3-trimethylpropane-1,3-diyl;

C₂-C₆-alkenediyl: ethene-1,1-diyl, ethene-1,2-diyl, 1-propene-1,1-diyl, 1-propene-1,2-diyl, 1-propene-1,3-diyl, 2-propene-1,1-diyl, 2-propene-1,2-diyl, 2-propene-1,3-diyl, 1-butene-1,1-diyl, 1-butene-1,2-diyl, 1-butene-1,3-diyl, 1-butene-1,4-diyl, 2-butene-1,1-diyl, 2-butene-1,2-diyl, 2-butene-1,3-diyl, 2-butene-1,4-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-methyl-1-propene-1,2-diyl, 1-methyl-1-propene-1,3-diyl, 1-methyl-2-propene-1,1-diyl, 1-methyl-2-propene-1,2-diyl, 1-methyl-2-propene-1,3-diyl, 2-methyl-1,1-propene-1,1-diyl, 2-methyl-1-propene-1,3-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-pentene-1,1-diyl, 1-pentene-1,2-diyl, 1-pentene-1,3-diyl, 1-pentene-1,4-diyl, 1-pentene-1,5-diyl, 1-hexene-1,1-diyl, 1-hexene-1,2-diyl, 1-hexene-1,3-diyl, 1-hexene-1,4-diyl, 1-hexene-1,5-diyl or 1-hexene-1,6-diyl;

C₂-C₆-alkadienediyl: 1,3-butadiene-1,1-diyl, 1,3-butadiene-1,2-diyl, 1,3-butadiene-1,3-diyl, 1,3-butadiene-1,4-diyl, 1,3-pentadiene-1,1-diyl, 1,3-pentadiene-1,2-diyl, 1,3-pentadiene-1,3-diyl, 1,3-pentadiene-1,4-diyl, 1,3-pentadiene-1,5-diyl, 2,4-pentadiene-1,1-diyl, 2,4-pentadiene-1,2-diyl, 2,4-pentadiene-1,3-diyl, 2,4-pentadiene-1,4-diyl, 2,4-pentadiene-1,5-diyl, 1-methyl-1,3-butadiene-1,4-diyl, 1,3-hexadiene-1,1-diyl, 1,3-hexadiene-1,2-diyl, 1,3-hexadiene-1,3-diyl, 1,3-hexadiene-1,4-diyl, 1,3-hexadiene-1,5-diyl, 1,3-hexadiene-1,6-diyl, 1-methyl-1,3-pentadiene-1,2-diyl, 1-methyl-1,3-pentadiene-1,3-diyl, 1-methyl-1,3-pentadiene-1,4-diyl or 1-methyl-1,3-pentadiene-1,5-diyl;

C₂-C₆-alkynediyl: ethyne-1,2-diyl, 1-propyne-1,3-diyl, 2-propyne-1,1-diyl, 2-propyne-1,3-diyl, 1-butyne-1,3-diyl, 1-butyne-1,4-diyl, 2-butyne-1,1-diyl, 2-butyne-1,4-diyl, 1-methyl-2-propyne-1,1-diyl, 1-methyl-2-propyne-1,3-diyl, 1-pentyne-1,3-diyl,-1-pentyne-1,4-diyl, 1-pentyne-1,5-diyl, 2-pentyne-1,1-diyl, 2-pentyne-1,4-diyl, 2-pentyne-1,5-diyl, 3-pentyne-1,1-diyl, 3-pentyne-1,2-diyl, 3-pentyne-1,5-diyl, 4-pentyne-1,1-diyl, 4-pentyne-1,2-diyl, 4-pentyne-1,3-diyl, 4-pentyne-1,5-diyl, 1-hexyne-1,3-diyl, 1-hexyne-1,4-diyl, 1-hexyne-1,5-diyl, 1-hexyne-1,6-diyl, 2-hexyne-1,1-diyl, 2-hexyne-1,4-diyl, 2-hexyne-1,5-diyl, 2-hexyne-1,6-diyl, 3-hexyne-1,1-diyl, 3-hexyne-1,2-diyl, 3-hexyne-1,5-diyl, 3-hexyne-1,6-diyl, 4-hexyne-1,1-diyl, 4-hexyne-1,2-diyl, 4-hexyne-1,3-diyl, 4-hexyne-1,6-diyl, 5-hexyne-1,1-diyl, 5-hexyne-1,2-diyl, 5-hexyne-1,3-diyl, 5-hexyne-1,4-diyl or 5-hexyne-1,6-diyl;

C₃-C₆-cycloalkyl, and the cycloalkyl moieties of C₃-C₆-cycloalkylamino and C₃-C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C₁-C₄-alkyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclyl-C₂-C₆-alkenylcarbonyl, heterocyclylcarbonyl-C₁-C₆-alkyl, N—(C₁-C₆-alkyl)—N-(heterocyclyl)aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which contains one, two, there or four identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example, C-bonded 5-membered rings such as:

tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-diokolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl, Δ³-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl, 1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl, 1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl, 1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl, 1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl, 1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl, 1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl, 1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl, 1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl, 1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl, 1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl, 1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl, 1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl, tetrazol-5-yl;

C-bonded 6-membered rings such as:

tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5 6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl, 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl or 1,2,4,5-tetrazin-3-yl;

N-bonded 5-membered rings such as:

tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl, 1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl, 1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl, 1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl, 1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl, 1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl;

N-bonded 6-membered rings such as:

piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl(morpholinyl), tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;

and also N-bonded cyclic imides such as:

phthalimide, tetrahydrophthalimide, succinimide, maleimide, glutarimide, 5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or 2,4-dioxo(1H,3H)pyrimidin-3-yl;

where, if appropriate, the sulfur of the heterocycles mentioned may be oxidized to S═O or S(═O)₂

and where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C₃-C₆-carbocycle or with a further 5- to 6-membered heterocycle.

All phenyl rings or heterocyclyl radicals and all phenyl components in phenoxy, phenylalkyl, phenylcarbonylalkyl, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl and N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl or phenoxysulfonyl or heterocyclyl components in heterocyclyloxy, heterocyclylalkyl, heterocyclylcarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl are, unless stated otherwise, preferably unsubstituted, or they carry one, two or three halogen atoms and/or a nitro group, a cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.

With respect to the use of the compounds of the formula I according to the invention as herbicides, the variables X, Y, R¹ to R¹⁶ preferably have the following meanings, in each case on their own or in combination:

R¹ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkyloxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxyalkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, particularly preferably methyl, chloro, methoxy, methylthio, methylsulfinyl, methylsulfonyl, bromomethyl, methoxymethyl, methylsulfonylmethyl;

R² is hydrogen, halogen, for example chlorine or bromine, C₁-C₆-alkyl, for example methyl;

X is C—R³ where R³ is as defined above, or is N;

Y is S, SO₂ or NR⁴ where R⁴ is as defined above;

Pz is a radical of the formula IIa, where R⁸, R⁹ and R¹⁰ are as defined above.

Preference is given, in particular, to compounds of the formula I where Y is O, S, SO₂ or N—R⁴ and X is C—R³. Preference is also given to compounds of the formula I where X is N and Y is S or N—R⁴.

R⁸, R⁹ and R¹⁰ independently of one another are preferably as defined below:

R⁸ is hydroxyl, halogen, OR¹¹, SR¹¹, SO₂R¹², OSO₂R¹², NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; in particular hydroxyl, OR¹¹ or OSO₂R¹², specifically hydroxyl, C₁-C₄-alkyloxy, O—CH₂-phenyl, phenylcarbonyloxy, 2-, 3- or 4-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, C₁-C₄-sulfonyloxy, phenylsulfonyloxy and 2-, 3- or 4-methylphenylsulfonyloxy;

R⁹ is C₁-C₆-alkyl, in particular C₁-C₄-alkyl, and R¹⁰ is hydrogen or C₁-C₄-alkyl, in particular hydrogen or C₁-C₄-alkyl.

Preference is also given to compounds where R⁹ is C₃-C₆-cycloalkyl, in particular cyclopropyl.

Particular preference is given to compounds of the formula I where X is C—R³ and

R³ is hydrogen, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkyl, is phenyl or pyridyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one, two or three, in particular one, of the following radicals: halogen, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, and C₁-C₄-haloalkoxy; or

is COOR⁵ where R⁵ is as defined above. Here, R⁵ is in particular hydrogen or C₁-C₆-alkyl and particularly preferably hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, isobutyl and tert-butyl.

Preference is also given to compounds I where R³ is C₃-C₆-cycloalkyl or phenoxy which may be substituted as stated for phenyl.

Examples of preferred radicals R³ are hydrogen, fluorine, chlorine, bromine, cyano, thiocyanato, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxymethyl, ethoxymethyl, methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy, 2-methylprop-1-oxy, tert-butyloxy, difluoromethyloxy, trifluoromethyloxy, 2,2,2-trifluoroethyl-1-oxy, (methoxy)methyloxy, methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, 1-butylsulfanyl, 2-butylsulfanyl, 2-methylprop-1-ylsulfanyl, tert-butylsulfanyl, fluoromethylsulfanyl, trifluoromethylsulfanyl, 2,2,2-trifluoroethyl-1-sulfanyl, 2-(methylcarbonyl)ethyl, phenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-hydroxyphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-(trifluoromethoxy)phenyl, 2-, 3- or 4-(difluoromethoxy)phenyl, 2-, 3- or 4-(trifluoromethyl)phenyl, 2-, 3- or 4-tolyl, 2-, 3- or 4-pyridinyl, 2-, 3- or 4-fluorophenoxy, 2-, 3- or 4-methoxyphenoxy, 2-, 3- or 4-trifluoromethylphenoxy, 2-, 3- or 4-chlorophenoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl and phenoxycarbonyl.

Very particularly preferred compounds of the formula I where X=C—R³ are those compounds where R³ is hydrogen, halogen, in particular fluorine or chlorine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, in particular fluoromethyl, difluoromethyl, trifluoromethyl and 2,2,2-trifluoroethyl, or phenyl or phenoxy where the phenyl or phenoxy radical may carry one, two or three, in particular one, substituent(s), selected from the group consisting of C₁-C₄-alkyl, in particular methyl, halogen, in particular fluorine or chlorine, C₁-C₄-alkoxy, in particular methoxy, or haloalkoxy, in particular trifluoromethoxy.

Among the pyrazole derivatives of the formula I mentioned above, particular preference is given to those compounds which are derived from benzothiazole-5-carboxylic acid, i.e. compounds of the formula I where X is a radical C—R³ and Y is selected from the group consisting of S, SO and SO₂. In turn, among the pyrazole derivatives of benzothiazole preference is given to those where R³ has one of the meanings mentioned above as being preferred. In particular, Y is S or SO₂.

Preference according to the invention is also given to those pyrazolyl derivatives which are derived from benzoxazole-5-carboxylic acid, i.e. compounds of the formula I where X is a group C—R³ where R³ is as defined above and Y is an oxygen atom. Among these, in turn, preference is given to those compounds where R³ has the meanings given above as being preferred.

Preference is also given to pyrazole derivatives of the formula I which are derived from benzimidazole-5-carboxylic acid, i.e. compounds of the formula I where X is C—R³, where R³ is as defined above, and Y is a group N—R⁴, where R⁴ is as defined above. Among these, preference is given to those benzimidazole derivatives of the formula I where R³ has the meanings given above as being preferred for R³. Furthermore, preference is given to benzimidazole derivatives of the formula I where R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl, in particular hydrogen, methyl, ethyl, n-propyl or isopropyl.

Preference according to the invention is also given to pyrazolyl derivatives of benzotriazole-5-carboxylic acid, i.e. compounds of the formula I where X is nitrogen and Y is a group N—R⁴, where R⁴ is as defined above. Among these, in turn, preference is given to those compounds where R⁴ has the meanings given above as being preferred.

Preference according to the invention is also given to pyrazolyl derivatives of benzothiadiazole-5-carboxylic acid, i.e. compounds of the formula I where X is N and Y is S. Preference is also given to pyrazole derivatives of benzoisothiadiazolecarboxylic acid, i.e. compounds of the formula I where X—Y is S═N and X is S.

Among the pyrazolyl derivatives of the formula I mentioned as being preferred, preference is, in turn, given to those compounds where Pz in the formula I is a group of the formula IIa. Among these, in turn, particular preference is given to compounds of the formula I where the variables R⁸, R⁹ and R¹⁰ in the formula IIa on their own, and particularly preferably in combination with one another, are as defined below:

R⁸ is hydroxyl, halogen, OR¹¹, SR¹¹, SO₂R¹², OSO₂R¹², NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, in particular hydroxyl, OR¹¹ and OSO₂R¹²;

R⁹ is C₁-C₄-alkyl or cyclopropyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl.

Among the compounds of the formula I where Pz is a pyrazolyl radical of the formula IIa, very particular preference is given to those compounds where the variables R⁸, R⁹ and R¹⁰ together have the following meanings:

R⁸ is hydroxyl, C₁-C₄-alkyloxy, O—CH₂-phenyl, phenylcarbonyloxy, 2-, 3- or 4-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, C₁-C₄-sulfonyloxy, phenylsulfonyloxy and 2-, 3- or 4-methylphenylsulfonyloxy;

R⁹ is C₁-C₄-alkyl or cyclopropyl and

R¹⁰ is hydrogen or C₁-C₄-alkyl.

Very particularly preferred radicals of the formula IIa are the radicals IIa1 to IIa90 given in Table 1.

TABLE 1 IIa

IIa R⁸ R⁹ R¹⁰ IIa1 OH CH₃ H IIa2 OCH₃ CH₃ H IIa3 OCH₂—C₆H₅ CH₃ H IIa4 OC(O)CH₃ CH₃ H IIa5 OC(O)C₆H₅ CH₃ H IIa6 OC(O)—(3-C₆H₄F) CH₃ H IIa7 OS(O)₂CH₃ CH₃ H IIa8 OS(O)₂—(4-C₆H₄CH₃) CH₃ H IIa9 OH C₂H₅ H IIa10 OCH₃ C₂H₅ H IIa11 OCH₂—C₆H₅ C₂H₅ H IIa12 OC(O)CH₃ C₂H₅ H IIa13 OC(O)C₆H₅ C₂H₅ H IIa14 OC(O)—(3-C₆H₄F) C₂H₅ H IIa15 OS(O)₂CH₃ C₂H₅ H IIa16 OS(O)₂—(4-C₆H₄CH₃) C₂H₅ H IIa17 OH i-C₃H₇ H IIa18 OCH₃ i-C₃H₇ H IIa19 OCH₂—C₆H₅ i-C₃H₇ H IIa20 OC(O)CH₃ i-C₃H₇ H IIa21 OC(O)C₆H₅ i-C₃H₇ H IIa22 OC(O)—(3-C₆H₄F) i-C₃H₇ H IIa23 OS(O)₂CH₃ i-C₃H₇ H IIa24 OS(O)₂—(4-C₆H₄CH₃) i-C₃H₇ H IIa25 OH t-C₄H₉ H IIa26 OCH₃ t-C₄H₉ H IIa27 OCH₂—C₆H₅ t-C₄H₉ H IIa28 OC(O)CH₃ t-C₄H₉ H IIa29 OC(O)C₆H₅ t-C₄H₉ H IIa30 OC(O)—(3-C₆H₄F) t-C₄H₉ H IIa31 OS(O)₂CH₃ t-C₄H₉ H IIa32 OS(O)₂—(4-C₆H₄CH₃) t-C₄H₉ H IIa33 OH CH₃ CH₃ IIa34 OCH₃ CH₃ CH₃ IIa35 OCH₂—C₆H₅ CH₃ CH₃ IIa36 OC(O)CH₃ CH₃ CH₃ IIa37 OC(O)C₆H₅ CH₃ CH₃ IIa38 OC(O)—(3-C₆H₄F) CH₃ CH₃ IIa39 OS(O)₂CH₃ CH₃ CH₃ IIa40 OS(O)₂—(4-C₆H₄CH₃) CH₃ CH₃ IIa41 OH C₂H₅ CH₃ IIa42 OCH₃ C₂H₅ CH₃ IIa43 OCH₂—C₆H₅ C₂H₅ CH₃ IIa44 OC(O)CH₃ C₂H₅ CH₃ IIa45 OC(O)C₆H₅ C₂H₅ CH₃ IIa46 OC(O)—(3-C₆H₄F) C₂H₅ CH₃ IIa47 OS(O)₂CH₃ C₂H₅ CH₃ IIa48 OS(O)₂—(4-C₆H₄CH₃) C₂H₅ CH₃ IIa49 OH i-C₃H₇ CH₃ IIa50 OCH₃ i-C₃H₇ CH₃ IIa51 OCH₂—C₆H₅ i-C₃H₇ CH₃ IIa52 OC(O)CH₃ i-C₃H₇ CH₃ IIa53 OC(O)C₆H₅ i-C₃H₇ CH₃ IIa54 OC(O)—(3-C₆H₄F) i-C₃H₇ CH₃ IIa55 OS(O)₂CH₃ i-C₃H₇ CH₃ IIa56 OS(O)₂—(4-C₆H₄CH₃) i-C₃H₇ CH₃ IIa57 OH t-C₄H₉ CH₃ IIa58 OCH₃ t-C₄H₉ CH₃ IIa59 OCH₂—C₆H₅ t-C₄H₉ CH₃ IIa60 OC(O)CH₃ t-C₄H₉ CH₃ IIa61 OC(O)C₆H₅ t-C₄H₉ CH₃ IIa62 OC(O)—(3-C₆H₄F) t-C₄H₉ CH₃ IIa63 OS(O)₂CH₃ t-C₄H₉ CH₃ IIa64 OS(O)₂—(4-C₆H₄CH₃) t-C₄H₉ CH₃ IIa65 OH c-C₃H₅ CH₃ IIa66 OCH₃ c-C₃H₅ CH₃ IIa67 OCH₂—C₆H₅ c-C₃H₅ CH₃ IIa68 OC(O)CH₃ c-C₃H₅ CH₃ IIa69 OC(O)C₆H₅ c-C₃H₅ CH₃ IIa70 OC(O)—(3-C₆H₄F) c-C₃H₅ CH₃ IIa71 OS(O)₂CH₃ c-C₃H₅ CH₃ IIa72 OS(O)₂—(4-C₆H₄CH₃) c-C₃H₅ CH₃ IIa73 OH c-C₃H₅ H IIa74 OCH₃ c-C₃H₅ H IIa75 OCH₂—C₆H₅ c-C₃H₅ H IIa76 OC(O)CH₃ c-C₃H₅ H IIa77 OC(O)C₆H₅ c-C₃H₅ H IIa78 OC(O)—(3-C₆H₄F) c-C₃H₅ H IIa79 OS(O)₂CH₃ c-C₃H₅ H IIa80 OS(O)₂—(4-C₆H₄CH₃) c-C₃H₅ H IIa81 OC(O)c-C₃H₅ CH₃ H IIa82 OC(O)-c-C₃H₅ C₂H₅ H IIa83 OC(O)-c-C₃H₅ i-C₃H₇ H IIa84 OC(O)-c-C₃H₅ t-C₄H₉ H IIa85 OC(O)-c-C₃H₅ c-C₃H₅ H IIa86 OC(O)-c-C₃H₅ CH₃ CH₃ IIa87 OC(O)-c-C₃H₅ C₂H₅ CH₃ IIa88 OC(O)-c-C₃H₅ i-C₃H₇ CH₃ IIa89 OC(O)-c-C₃H₅ t-C₄H₉ CH₃ IIa90 OC(O)-c-C₃H₅ c-C₃H₅ CH₃ i-C₃H₇: isopropyl c-C₃H₅: cyclopropyl t-C₄H₉: tertiary butyl C₆H₅: phenyl 3-C₆H₄F: 3-fluorophenyl 4-C₆H₄CH₃: 4-methylphenyl

TABLE A Particularly preferred combinations of R¹, R² and R³ R³ R¹ R² 1 H CH₃ CH₃ 2 F CH₃ CH₃ 3 Cl CH₃ CH₃ 4 Br CH₃ CH₃ 5 OH CH₃ CH₃ 6 SH CH₃ CH₃ 7 NH₂ CH₃ CH₃ 8 CN CH₃ CH₃ 9 NO₂ CH₃ CH₃ 10 SCN CH₃ CH₃ 11 NH—NH₂ CH₃ CH₃ 12 CH₃ CH₃ CH₃ 13 C₂H₅ CH₃ CH₃ 14 n-C₃H₇ CH₃ CH₃ 15 i-C₃H₇ CH₃ CH₃ 16 n-C₄H₉ CH₃ CH₃ 17 s-C₄H₉ CH₃ CH₃ 18 i-C₄H₉ CH₃ CH₃ 19 t-C₄H₉ CH₃ CH₃ 20 CH₂Cl CH₃ CH₃ 21 CHCl₂ CH₃ CH₃ 22 CCl₃ CH₃ CH₃ 23 CH₂F CH₃ CH₃ 24 CHF₂ CH₃ CH₃ 25 CF₃ CH₃ CH₃ 26 CH₂CF₃ CH₃ CH₃ 27 CH₂OCH₃ CH₃ CH₃ 28 CH₂OCH₂CH₃ CH₃ CH₃ 29 CH₂NH₂ CH₃ CH₃ 30 OCH₃ CH₃ CH₃ 31 OC₂H₅ CH₃ CH₃ 32 O-n-C₃H₇ CH₃ CH₃ 33 O-i-C₃H₇ CH₃ CH₃ 34 O-n-C₄H₉ CH₃ CH₃ 35 O-s-C₄H₉ CH₃ CH₃ 36 O-i-C₄H₉ CH₃ CH₃ 37 O-t-C₄H₉ CH₃ CH₃ 38 OCHF₂ CH₃ CH₃ 39 OCF₃ CH₃ CH₃ 40 OCH₂CF₃ CH₃ CH₃ 41 OCH₂OCH₃ CH₃ CH₃ 42 SCH₃ CH₃ CH₃ 43 SC₂H₅ CH₃ CH₃ 44 S-n-C₃H₇ CH₃ CH₃ 45 S-i-C₃H₇ CH₃ CH₃ 46 S-n-C₄H₉ CH₃ CH₃ 47 S-s-C₄H₉ CH₃ CH₃ 48 S-i-C₄H₉ CH₃ CH₃ 49 S-t-C₄H₉ CH₃ CH₃ 50 SCHF₂ CH₃ CH₃ 51 SCF₃ CH₃ CH₃ 52 SCH₂CF₃ CH₃ CH₃ 53 SCH₂OCH₃ CH₃ CH₃ 54 NHCH₃ CH₃ CH₃ 55 NHC₂H₅ CH₃ CH₃ 56 NH-phenyl CH₃ CH₃ 57 N(CH₃)₂ CH₃ CH₃ 58 N(CH₂CH₃)₂ CH₃ CH₃ 59 N(phenyl)₂ CH₃ CH₃ 60 (CH₂)₂COCH₃ CH₃ CH₃ 61 phenyl CH₃ CH₃ 62 2-F-phenyl CH₃ CH₃ 63 3-F-phenyl CH₃ CH₃ 64 4-F-phenyl CH₃ CH₃ 65 2-Cl-phenyl CH₃ CH₃ 66 3-Cl-phenyl CH₃ CH₃ 67 4-Cl-phenyl CH₃ CH₃ 68 2-OH-phenyl CH₃ CH₃ 69 3-OH-phenyl CH₃ CH₃ 70 4-OH-phenyl CH₃ CH₃ 71 2-OCH₃-phenyl CH₃ CH₃ 72 3-OCH₃-phenyl CH₃ CH₃ 73 4-OCH₃-phenyl CH₃ CH₃ 74 2-OCH₃-phenyl CH₃ CH₃ 75 3-OCF₃-phenyl CH₃ CH₃ 76 4-OCF₃-phenyl CH₃ CH₃ 77 2-OCHF₂-phenyl CH₃ CH₃ 78 3-OCHF₂-phenyl CH₃ CH₃ 79 4-OCHF₂-phenyl CH₃ CH₃ 80 2-CF₃-phenyl CH₃ CH₃ 81 3-CF₃-phenyl CH₃ CH₃ 82 4-CF₃-phenyl CH₃ CH₃ 83 2-CH₃-phenyl CH₃ CH₃ 84 3-CH₃-phenyl CH₃ CH₃ 85 4-CH₃-phenyl CH₃ CH₃ 86 2-NO₂-phenyl CH₃ CH₃ 87 3-NO₂-phenyl CH₃ CH₃ 88 4-NO₂-phenyl CH₃ CH₃ 89 2-pyridyl CH₃ CH₃ 90 3-pyridyl CH₃ CH₃ 91 4-pyridyl CH₃ CH₃ 92 3′-CH₃-2-pyridyl CH₃ CH₃ 93 4′-CH₃-2-pyridyl CH₃ CH₃ 94 5′-CH₃-2-pyridyl CH₃ CH₃ 95 6′-CH₃-2-pyridyl CH₃ CH₃ 96 2′-CH₃-3-pyridyl CH₃ CH₃ 97 4′-CH₃-3-pyridyl CH₃ CH₃ 98 5′-CH₃-3-pyridyl CH₃ CH₃ 99 6′-CH₃-3-pyridyl CH₃ CH₃ 100 2′-CH₃-4-pyridyl CH₃ CH₃ 101 3′-CH₃-4-pyridyl CH₃ CH₃ 102 3′-Cl-2-pyridyl CH₃ CH₃ 103 4′-Cl-2-pyridyl CH₃ CH₃ 104 5′-Cl-2-pyridyl CH₃ CH₃ 105 6′-Cl-2-pyridyl CH₃ CH₃ 106 2′-Cl-3-pyridyl CH₃ CH₃ 107 4′-Cl-3-pyridyl CH₃ CH₃ 108 5′-Cl-3-pyridyl CH₃ CH₃ 109 6′-Cl-3-pyridyl CH₃ CH₃ 110 2′-Cl-4-pyridyl CH₃ CH₃ 111 3′-Cl-4-pyridyl CH₃ CH₃ 112 cyclohexylamino CH₃ CH₃ 113 cyclopentylamino CH₃ CH₃ 114 morpholino CH₃ CH₃ 115 CO₂H CH₃ CH₃ 116 CO₂CH₃ CH₃ CH₃ 117 CO₂C₂H₅ CH₃ CH₃ 118 CO₂-n-C₃H₇ CH₃ CH₃ 119 CO₂-i-C₃H₇ CH₃ CH₃ 120 CO₂-n-C₄H₉ CH₃ CH₃ 121 CO₂-s-C₄H₉ CH₃ CH₃ 122 CO₂-i-C₄H₉ CH₃ CH₃ 123 CO₂-t-C₄H₉ CH₃ CH₃ 124 CO₂-Ph CH₃ CH₃ 125 CO₂-3-pyridyl CH₃ CH₃ 126 CONHCH₃ CH₃ CH₃ 127 CONHC₂H₅ CH₃ CH₃ 128 CONHPh CH₃ CH₃ 129 CON(CH₃)₂ CH₃ CH₃ 130 CON(CH₂CH₃)₂ CH₃ CH₃ 131 CON(phenyl)₂ CH₃ CH₃ 132 H OCH₃ CH₃ 133 F OCH₃ CH₃ 134 Cl OCH₃ CH₃ 135 Br OCH₃ CH₃ 136 OH OCH₃ CH₃ 137 SH OCH₃ CH₃ 138 NH₂ OCH₃ CH₃ 139 CN OCH₃ CH₃ 140 NO₂ OCH₃ CH₃ 141 SCN OCH₃ CH₃ 142 NH—NH₂ OCH₃ CH₃ 143 CH₃ OCH₃ CH₃ 144 C₂H₅ OCH₃ CH₃ 145 n-C₃H₇ OCH₃ CH₃ 146 i-C₃H₇ OCH₃ CH₃ 147 n-C₄H₉ OCH₃ CH₃ 148 s-C₄H₉ OCH₃ CH₃ 149 i-C₄H₉ OCH₃ CH₃ 150 t-C₄H₉ OCH₃ CH₃ 151 CH₂Cl OCH₃ CH₃ 152 CHCl₂ OCH₃ CH₃ 153 CCl₃ OCH₃ CH₃ 154 CH₂F OCH₃ CH₃ 155 CHF₂ OCH₃ CH₃ 156 CF₃ OCH₃ CH₃ 157 CH₂CF₃ OCH₃ CH₃ 158 CH₂OCH₃ OCH₃ CH₃ 159 CH₂OCH₂CH₃ OCH₃ CH₃ 160 CH₂NH₂ OCH₃ CH₃ 161 OCH₃ OCH₃ CH₃ 162 OC₂H₅ OCH₃ CH₃ 163 O-n-C₃H₇ OCH₃ CH₃ 164 O-i-C₃H₇ OCH₃ CH₃ 165 O-n-C₄H₉ OCH₃ CH₃ 166 O-s-C₄H₉ OCH₃ CH₃ 167 O-i-C₄H₉ OCH₃ CH₃ 168 O-t-C₄H₉ OCH₃ CH₃ 169 OCHF₂ OCH₃ CH₃ 170 OCF₃ OCH₃ CH₃ 171 OCH₂CF₃ OCH₃ CH₃ 172 OCH₂OCH₃ OCH₃ CH₃ 173 SCH₃ OCH₃ CH₃ 174 SC₂H₅ OCH₃ CH₃ 175 S-n-C₃H₇ OCH₃ CH₃ 176 S-i-C₃H₇ OCH₃ CH₃ 177 S-n-C₄H₉ OCH₃ CH₃ 178 S-s-C₄H₉ OCH₃ CH₃ 179 S-i-C₄H₉ OCH₃ CH₃ 180 S-t-C₄H₉ OCH₃ CH₃ 181 SCHF₂ OCH₃ CH₃ 182 SCF₃ OCH₃ CH₃ 183 SCH₂CF₃ OCH₃ CH₃ 184 SCH₂OCH₃ OCH₃ CH₃ 185 NHCH₃ OCH₃ CH₃ 186 NHC₂H₅ OCH₃ CH₃ 187 NHphenyl OCH₃ CH₃ 188 N(CH₃)₂ OCH₃ CH₃ 189 N(CH₂CH₃)₂ OCH₃ CH₃ 190 N(phenyl)₂ OCH₃ CH₃ 191 (CH₂)₂COCH₃ OCH₃ CH₃ 192 phenyl OCH₃ CH₃ 193 2-F-phenyl OCH₃ CH₃ 194 3-F-phenyl OCH₃ CH₃ 195 4-F-phenyl OCH₃ CH₃ 196 2-Cl-phenyl OCH₃ CH₃ 197 3-Cl-phenyl OCH₃ CH₃ 198 4-Cl-phenyl OCH₃ CH₃ 199 2-OH-phenyl OCH₃ CH₃ 200 3-OH-phenyl OCH₃ CH₃ 201 4-OH-phenyl OCH₃ CH₃ 202 2-OCH₃-phenyl OCH₃ CH₃ 203 3-OCH₃-phenyl OCH₃ CH₃ 204 4-OCH₃-phenyl OCH₃ CH₃ 205 2-OCF₃-phenyl OCH₃ CH₃ 206 3-OCF₃-phenyl OCH₃ CH₃ 207 4-OCF₃-phenyl OCH₃ CH₃ 208 2-OCHF₂-phenyl OCH₃ CH₃ 209 3-OCHF₂-phenyl OCH₃ CH₃ 210 4-OCHF₂-phenyl OCH₃ CH₃ 211 2-CF₃-phenyl OCH₃ CH₃ 212 3-CF₃-phenyl OCH₃ CH₃ 213 4-CF₃-phenyl OCH₃ CH₃ 214 2-CH₃-phenyl OCH₃ CH₃ 215 3-CH₃-phenyl OCH₃ CH₃ 216 4-CH₃-phenyl OCH₃ CH₃ 217 2-NO₂-phenyl OCH₃ CH₃ 218 3-NO₂-phenyl OCH₃ CH₃ 219 4-NO₂-phenyl OCH₃ CH₃ 220 2-pyridyl OCH₃ CH₃ 221 3-pyridyl OCH₃ CH₃ 222 4-pyridyl OCH₃ CH₃ 223 3′-CH₃-2-pyridyl OCH₃ CH₃ 224 4′-CH₃-2-pyridyl OCH₃ CH₃ 225 5′-CH₃-2-pyridyl OCH₃ CH₃ 226 6′-CH₃-2-pyridyl OCH₃ CH₃ 227 2′-CH₃-3-pyridyl OCH₃ CH₃ 228 4′-CH₃-3-pyridyl OCH₃ CH₃ 229 5′-CH₃-3-pyridyl OCH₃ CH₃ 230 6′-CH₃-3-pyridyl OCH₃ CH₃ 231 2′-CH₃-4-pyridyl OCH₃ CH₃ 232 3′-CH₃-4-pyridyl OCH₃ CH₃ 233 3′-Cl-2-pyridyl OCH₃ CH₃ 234 4′-Cl-2-pyridyl OCH₃ CH₃ 235 5′-Cl-2-pyridyl OCH₃ CH₃ 236 6′-Cl-2-pyridyl OCH₃ CH₃ 237 2′-Cl-3-pyridyl OCH₃ CH₃ 238 4′-Cl-3-pyridyl OCH₃ CH₃ 239 5′-Cl-3-pyridyl OCH₃ CH₃ 240 6′-Cl-3-pyridyl OCH₃ CH₃ 241 2′-Cl-4-pyridyl OCH₃ CH₃ 242 3′-Cl-4-pyridyl OCH₃ CH₃ 243 cyclohexylamino OCH₃ CH₃ 244 cyclopentylamino OCH₃ CH₃ 245 morpholino OCH₃ CH₃ 246 CO₂H OCH₃ CH₃ 247 CO₂CH₃ OCH₃ CH₃ 248 CO₂C₂H₅ OCH₃ CH₃ 249 CO₂-n-C₃H₇ OCH₃ CH₃ 250 CO₂-i-C₃H₇ OCH₃ CH₃ 251 CO₂-n-C₄H₉ OCH₃ CH₃ 252 CO₂-s-C₄H₉ OCH₃ CH₃ 253 CO₂-i-C₄H₉ OCH₃ CH₃ 254 CO₂-t-C₄H₉ OCH₃ CH₃ 255 CO₂-Ph OCH₃ CH₃ 256 CO₂-3-pyridyl OCH₃ CH₃ 257 CONHCH₃ OCH₃ CH₃ 258 CONHC₂H₅ OCH₃ CH₃ 259 CONHphenyl OCH₃ CH₃ 260 CON(CH₃)₂ OCH₃ CH₃ 261 CON(CH₂CH₃)₂ OCH₃ CH₃ 262 CON(phenyl)₂ OCH₃ CH₃ 263 H Cl CH₃ 264 F Cl CH₃ 265 Cl Cl CH₃ 266 Br Cl CH₃ 267 OH Cl CH₃ 268 SH Cl CH₃ 269 NH₂ Cl CH₃ 270 CN Cl CH₃ 271 NO₂ Cl CH₃ 272 SCN Cl CH₃ 273 NH—NH₂ Cl CH₃ 274 CH₃ Cl CH₃ 275 C₂H₅ Cl CH₃ 276 n-C₃H₇ Cl CH₃ 277 i-C₃H₇ Cl CH₃ 278 n-C₄H₉ Cl CH₃ 279 s-C₄H₉ Cl CH₃ 280 i-C₄H₉ Cl CH₃ 281 t-C₄H₉ Cl CH₃ 282 CH₂Cl Cl CH₃ 283 CHCl₂ Cl CH₃ 284 CCl₃ Cl CH₃ 285 CH₂F Cl CH₃ 286 CHF₂ Cl CH₃ 287 CF₃ Cl CH₃ 288 CH₂CF₃ Cl CH₃ 289 CH₂OCH₃ Cl CH₃ 290 CH₂OCH₂CH₃ Cl CH₃ 291 CH₂NH₂ Cl CH₃ 292 OCH₃ Cl CH₃ 293 OC₂H₅ Cl CH₃ 294 O-n-C₃H₇ Cl CH₃ 295 O-i-C₃H₇ Cl CH₃ 296 O-n-C₄H₉ Cl CH₃ 297 O-s-C₄H₉ Cl CH₃ 298 O-i-C₄H₉ Cl CH₃ 299 O-t-C₄H₉ Cl CH₃ 300 OCHF₂ Cl CH₃ 301 OCF₃ Cl CH₃ 302 OCH₂CF₃ Cl CH₃ 303 OCH₂OCH₃ Cl CH₃ 304 SCH₃ Cl CH₃ 305 SC₂H₅ Cl CH₃ 306 S-n-C₃H₇ Cl CH₃ 307 S-i-C₃H₇ Cl CH₃ 308 S-n-C₄H₉ Cl CH₃ 309 S-s-C₄H₉ Cl CH₃ 310 S-i-C₄H₉ Cl CH₃ 311 S-t-C₄H₉ Cl CH₃ 312 SCHF₂ Cl CH₃ 313 SCF₃ Cl CH₃ 314 SCH₂CF₃ Cl CH₃ 315 SCH₂OCH₃ Cl CH₃ 316 NHCH₃ Cl CH₃ 317 NHC₂H₅ Cl CH₃ 318 NH-phenyl Cl CH₃ 319 N(CH₃)₂ Cl CH₃ 320 N(CH₂CH₃)₂ Cl CH₃ 321 N(phenyl)₂ Cl CH₃ 322 (CH₂)₂COCH₃ Cl CH₃ 323 phenyl Cl CH₃ 324 2-F-phenyl Cl CH₃ 325 3-F-phenyl Cl CH₃ 326 4-F-phenyl Cl CH₃ 327 2-Cl-phenyl Cl CH₃ 328 3-Cl-phenyl Cl CH₃ 329 4-Cl-phenyl Cl CH₃ 330 2-OH-phenyl Cl CH₃ 331 3-OH-phenyl Cl CH₃ 332 4-OH-phenyl Cl CH₃ 333 2-OCH₃-phenyl Cl CH₃ 334 3-OCH₃-phenyl Cl CH₃ 335 4-OCH₃-phenyl Cl CH₃ 336 2-OCF₃-phenyl Cl CH₃ 337 3-OCF₃-phenyl Cl CH₃ 338 4-OCF₃-phenyl Cl CH₃ 339 2-OCHF₂-phenyl Cl CH₃ 340 3-OCHF₂-phenyl Cl CH₃ 341 4-OCHF₂-phenyl Cl CH₃ 342 2-CF₃-phenyl Cl CH₃ 343 3-CF₃-phenyl Cl CH₃ 344 4-CF₃-phenyl Cl CH₃ 345 2-CH₃-phenyl Cl CH₃ 346 3-CH₃-phenyl Cl CH₃ 347 4-CH₃-phenyl Cl CH₃ 348 2-NO₂-phenyl Cl CH₃ 349 3-NO₂-phenyl Cl CH₃ 350 4-NO₂-phenyl Cl CH₃ 351 2-pyridyl Cl CH₃ 352 3-pyridyl Cl CH₃ 353 4-pyridyl Cl CH₃ 354 3′-CH₃-2-pyridyl Cl CH₃ 355 4′-CH₃-2-pyridyl Cl CH₃ 356 5′-CH₃-2-pyridyl Cl CH₃ 357 6′-CH₃-2-pyridyl Cl CH₃ 358 2′-CH₃-3-pyridyl Cl CH₃ 359 4′-CH₃-3-pyridyl Cl CH₃ 360 5′-CH₃-3-pyridyl Cl CH₃ 361 6′-CH₃-3-pyridyl Cl CH₃ 362 2′-CH₃-4-pyridyl Cl CH₃ 363 3′-CH₃-4-pyridyl Cl CH₃ 364 3′-Cl-2-pyridyl Cl CH₃ 365 4′-Cl-2-pyridyl Cl CH₃ 366 5′-Cl-2-pyridyl Cl CH₃ 367 6′-Cl-2-pyridyl Cl CH₃ 368 2′-Cl-3-pyridyl Cl CH₃ 369 4′-Cl-3-pyridyl Cl CH₃ 370 5′-Cl-3-pyridyl Cl CH₃ 371 6′-Cl-3-pyridyl Cl CH₃ 372 2′-Cl-4-pyridyl Cl CH₃ 373 3′-Cl-4-pyridyl Cl CH₃ 374 cyclohexylamino Cl CH₃ 375 cyclopentylamino Cl CH₃ 376 morpholino Cl CH₃ 377 CO₂H Cl CH₃ 378 CO₂CH₃ Cl CH₃ 379 CO₂C₂H₅ Cl CH₃ 380 CO₂-n-C₃H₇ Cl CH₃ 381 CO₂-i-C₃H₇ Cl CH₃ 382 CO₂-n-C₄H₉ Cl CH₃ 383 CO₂-s-C₄H₉ Cl CH₃ 384 CO₂-i-C₄H₉ Cl CH₃ 385 CO₂-t-C₄H₉ Cl CH₃ 386 CO₂-phenyl Cl CH₃ 387 CO₂-3-pyridyl Cl CH₃ 388 CONHCH₃ Cl CH₃ 389 CONHC₂H₅ Cl CH₃ 390 CONH-phenyl Cl CH₃ 391 CON(CH₃)₂ Cl CH₃ 392 CON(CH₂CH₃)₂ Cl CH₃ 393 CON(phenyl)₂ Cl CH₃ 394 H CH₃ H 395 F CH₃ H 396 Cl CH₃ H 397 Br CH₃ H 398 OH CH₃ H 399 SH CH₃ H 400 NH₂ CH₃ H 401 CN CH₃ H 402 NO₂ CH₃ H 403 SCN CH₃ H 404 NH—NH₂ CH₃ H 405 CH₃ CH₃ H 406 C₂H₅ CH₃ H 407 n-C₃H₇ CH₃ H 408 i-C₃H₇ CH₃ H 409 n-C₄H₉ CH₃ H 410 s-C₄H₉ CH₃ H 411 i-C₄H₉ CH₃ H 412 t-C₄H₉ CH₃ H 413 CH₂Cl CH₃ H 414 CHCl₂ CH₃ H 415 CCl₃ CH₃ H 416 CH₂F CH₃ H 417 CHF₂ CH₃ H 418 CF₃ CH₃ H 419 CH₂CF₃ CH₃ H 420 CH₂OCH₃ CH₃ H 421 CH₂OCH₂CH₃ CH₃ H 422 CH₂NH₂ CH₃ H 423 OCH₃ CH₃ H 424 OC₂H₅ CH₃ H 425 O-n-C₃H₇ CH₃ H 426 O-i-C₃H₇ CH₃ H 427 O-n-C₄H₉ CH₃ H 428 O-s-C₄H₉ CH₃ H 429 O-i-C₄H₉ CH₃ H 430 O-t-C₄H₉ CH₃ H 431 OCHF₂ CH₃ H 432 OCF₃ CH₃ H 433 OCH₂CF₃ CH₃ H 434 OCH₂OCH₃ CH₃ H 435 SCH₃ CH₃ H 436 SC₂H₅ CH₃ H 437 S-n-C₃H₇ CH₃ H 438 S-i-C₃H₇ CH₃ H 439 S-n-C₄H₉ CH₃ H 440 S-s-C₄H₉ CH₃ H 441 S-i-C₄H₉ CH₃ H 442 S-t-C₄H₉ CH₃ H 443 SCHF₂ CH₃ H 444 SCF₃ CH₃ H 445 SCH₂CF₃ CH₃ H 446 SCH₂OCH₃ CH₃ H 447 NHCH₃ CH₃ H 448 NHC₂H₅ CH₃ H 449 NH-phenyl CH₃ H 450 N(CH₃)₂ CH₃ H 451 N(CH₂CH₃)₂ CH₃ H 452 N(phenyl)₂ CH₃ H 453 (CH₂)₂COCH₃ CH₃ H 454 phenyl CH₃ H 455 2-F-phenyl CH₃ H 456 3-F-phenyl CH₃ H 457 4-F-phenyl CH₃ H 458 2-Cl-phenyl CH₃ H 459 3-Cl-phenyl CH₃ H 460 4-Cl-phenyl CH₃ H 461 2-OH-phenyl CH₃ H 462 3-OH-phenyl CH₃ H 463 4-OH-phenyl CH₃ H 464 2-OCH₃-phenyl CH₃ H 465 3-OCH₃-phenyl CH₃ H 466 4-OCH₃-phenyl CH₃ H 467 2-OCF₃-phenyl CH₃ H 468 3-OCF₃-phenyl CH₃ H 469 4-OCF₃-phenyl CH₃ H 470 2-OCHF₂-phenyl CH₃ H 471 3-OCHF₂-phenyl CH₃ H 472 4-OCHF₂-phenyl CH₃ H 473 2-CF₃-phenyl CH₃ H 474 3-CF₃-phenyl CH₃ H 475 4-CF₃-phenyl CH₃ H 476 2-CH₃-phenyl CH₃ H 477 3-CH₃-phenyl CH₃ H 478 4-CH₃-phenyl CH₃ H 479 2-NO₂-phenyl CH₃ H 480 3-NO₂-phenyl CH₃ H 481 4-NO₂-phenyl CH₃ H 482 2-pyridyl CH₃ H 483 3-pyridyl CH₃ H 484 4-pyridyl CH₃ H 485 3′-CH₃-2-pyridyl CH₃ H 486 4′-CH₃-2-pyridyl CH₃ H 487 5′-CH₃-2-pyridyl CH₃ H 488 6′-CH₃-2-pyridyl CH₃ H 489 2′-CH₃-3-pyridyl CH₃ H 490 4′-CH₃-3-pyridyl CH₃ H 491 5′-CH₃-3-pyridyl CH₃ H 492 6′-CH₃-3-pyridyl CH₃ H 493 2′-CH₃-4-pyridyl CH₃ H 494 3′-CH₃-4-pyridyl CH₃ H 495 3′-Cl-2-pyridyl CH₃ H 496 4′-Cl-2-pyridyl CH₃ H 497 5′-Cl-2-pyridyl CH₃ H 498 6′-Cl-2-pyridyl CH₃ H 499 2′-Cl-3-pyridyl CH₃ H 500 4′-Cl-3-pyridyl CH₃ H 501 5′-Cl-3-pyridyl CH₃ H 502 6′-Cl-3-pyridyl CH₃ H 503 2′-Cl-4-pyridyl CH₃ H 504 3′-Cl-4-pyridyl CH₃ H 505 cyclohexylamino CH₃ H 506 cyclopentylamino CH₃ H 507 morpholino CH₃ H 508 CO₂H CH₃ H 509 CO₂CH₃ CH₃ H 510 CO₂C₂H₅ CH₃ H 511 CO₂-n-C₃H₇ CH₃ H 512 CO₂-i-C₃H₇ CH₃ H 513 CO₂-n-C₄H₉ CH₃ H 514 CO₂-s-C₄H₉ CH₃ H 515 CO₂-i-C₄H₉ CH₃ H 516 CO₂-t-C₄H₉ CH₃ H 517 CO₂-Ph CH₃ H 518 CO₂-3-pyridyl CH₃ H 519 CONHCH₃ CH₃ H 520 CONHC₂H₅ CH₃ H 521 CONH-phenyl CH₃ H 522 CON(CH₃)₂ CH₃ H 523 CON(CH₂CH₃)₂ CH₃ H 524 CON(phenyl)₂ CH₃ H 525 H OCH₃ H 526 F OCH₃ H 527 Cl OCH₃ H 528 Br OCH₃ H 529 OH OCH₃ H 530 SH OCH₃ H 531 NH₂ OCH₃ H 532 CN OCH₃ H 533 NO₂ OCH₃ H 534 SCN OCH₃ H 535 NH—NH₂ OCH₃ H 536 CH₃ OCH₃ H 537 C₂H₅ OCH₃ H 538 n-C₃H₇ OCH₃ H 539 i-C₃H₇ OCH₃ H 540 n-C₄H₉ OCH₃ H 541 s-C₄H₉ OCH₃ H 542 i-C₄H₉ OCH₃ H 543 t-C₄H₉ OCH₃ H 544 CH₂Cl OCH₃ H 545 CHCl₂ OCH₃ H 546 CCl₃ OCH₃ H 547 CH₂F OCH₃ H 548 CHF₂ OCH₃ H 549 CF₃ OCH₃ H 550 CH₂CF₃ OCH₃ H 551 CH₂OCH₃ OCH₃ H 552 CH₂OCH₂CH₃ OCH₃ H 553 CH₂NH₂ OCH₃ H 554 OCH₃ OCH₃ H 555 OC₂H₅ OCH₃ H 556 O-n-C₃H₇ OCH₃ H 557 O-i-C₃H₇ OCH₃ H 558 O-n-C₄H₉ OCH₃ H 559 O-s-C₄H₉ OCH₃ H 560 O-i-C₄H₉ OCH₃ H 561 O-t-C₄H₉ OCH₃ H 562 OCHF₂ OCH₃ H 563 OCF₃ OCH₃ H 564 OCH₂CF₃ OCH₃ H 565 OCH₂OCH₃ OCH₃ H 566 SCH₃ OCH₃ H 567 SC₂H₅ OCH₃ H 568 S-n-C₃H₇ OCH₃ H 569 S-i-C₃H₇ OCH₃ H 570 S-n-C₄H₉ OCH₃ H 571 S-s-C₄H₉ OCH₃ H 572 S-i-C₄H₉ OCH₃ H 573 S-t-C₄H₉ OCH₃ H 574 SCHF₂ OCH₃ H 575 SCF₃ OCH₃ H 576 SCH₂CF₃ OCH₃ H 577 SCH₂OCH₃ OCH₃ H 578 NHCH₃ OCH₃ H 579 NHC₂H₅ OCH₃ H 580 NHPh OCH₃ H 581 N(CH₃)₂ OCH₃ H 582 N(CH₂CH₃)₂ OCH₃ H 583 N(phenyl)₂ OCH₃ H 584 (CH₂)₂COCH₃ OCH₃ H 585 phenyl OCH₃ H 586 2-F-phenyl OCH₃ H 587 3-F-phenyl OCH₃ H 588 4-F-phenyl OCH₃ H 589 2-Cl-phenyl OCH₃ H 590 3-Cl-phenyl OCH₃ H 591 4-Cl-phenyl OCH₃ H 592 2-OH-phenyl OCH₃ H 593 3-OH-phenyl OCH₃ H 594 4-OH-phenyl OCH₃ H 595 2-OCH₃-phenyl OCH₃ H 596 3-OCH₃-phenyl OCH₃ H 597 4-OCH₃-phenyl OCH₃ H 598 2-OCF₃-phenyl OCH₃ H 599 3-OCF₃-phenyl OCH₃ H 600 4-OCF₃-phenyl OCH₃ H 601 2-OCHF₂-phenyl OCH₃ H 602 3-OCHF₂-phenyl OCH₃ H 603 4-OCHF₂-phenyl OCH₃ H 604 2-CF₃-phenyl OCH₃ H 605 3-CF₃-phenyl OCH₃ H 606 4-CF₃-phenyl OCH₃ H 607 2-CH₃-phenyl OCH₃ H 608 3-CH₃-phenyl OCH₃ H 609 4-CH₃-phenyl OCH₃ H 610 2-NO₂-phenyl OCH₃ H 611 3-NO₂-phenyl OCH₃ H 612 4-NO₂-phenyl OCH₃ H 613 2-pyridyl OCH₃ H 614 3-pyridyl OCH₃ H 615 4-pyridyl OCH₃ H 616 3′-CH₃-2-pyridyl OCH₃ H 617 4′-CH₃-2-pyridyl OCH₃ H 618 5′-CH₃-2-pyridyl OCH₃ H 619 6′-CH₃-2-pyridyl OCH₃ H 620 2′-CH₃-3-pyridyl OCH₃ H 621 4′-CH₃-3-pyridyl OCH₃ H 622 5′-CH₃-3-pyridyl OCH₃ H 623 6′-CH₃-3-pyridyl OCH₃ H 624 2′-CH₃-4-pyridyl OCH₃ H 625 3′-CH₃-4-pyridyl OCH₃ H 626 3′-Cl-2-pyridyl OCH₃ H 627 4′-Cl-2-pyridyl OCH₃ H 628 5′-Cl-2-pyridyl OCH₃ H 629 6′-Cl-2-pyridyl OCH₃ H 630 2′-Cl-3-pyridyl OCH₃ H 631 4′-Cl-3-pyridyl OCH₃ H 632 5′-Cl-3-pyridyl OCH₃ H 633 6′-Cl-3-pyridyl OCH₃ H 634 2′-Cl-4-pyridyl OCH₃ H 635 3′-Cl-4-pyridyl OCH₃ H 636 cyclohexylamino OCH₃ H 637 cyclopentylamino OCH₃ H 638 morpholino OCH₃ H 639 CO₂H OCH₃ H 640 CO₂CH₃ OCH₃ H 641 CO₂C₂H₅ OCH₃ H 642 CO₂-n-C₃H₇ OCH₃ H 643 CO₂-i-C₃H₇ OCH₃ H 644 CO₂-n-C₄H₉ OCH₃ H 645 CO₂-s-C₄H₉ OCH₃ H 646 CO₂-i-C₄H₉ OCH₃ H 647 CO₂-t-C₄H₉ OCH₃ H 648 CO₂-Ph OCH₃ H 649 CO₂-3-pyridyl OCH₃ H 650 CONHCH₃ OCH₃ H 651 CONHC₂H₅ OCH₃ H 652 CONH-phenyl OCH₃ H 653 CON(CH₃)₂ OCH₃ H 654 CON(CH₂CH₃)₂ OCH₃ H 655 CON(phenyl)₂ OCH₃ H 656 H Cl H 657 F Cl H 658 Cl Cl H 659 Br Cl H 660 OH Cl H 661 SH Cl H 662 NH₂ Cl H 663 CN Cl H 664 NO₂ Cl H 665 SCN Cl H 666 NH—NH₂ Cl H 667 CH₃ Cl H 668 C₂H₅ Cl H 669 n-C₃H₇ Cl H 670 i-C₃H₇ Cl H 671 n-C₄H₉ Cl H 672 s-C₄H₉ Cl H 673 i-C₄H₉ Cl H 674 t-C₄H₉ Cl H 675 CH₂Cl Cl H 676 CHCl₂ Cl H 677 CCl₃ Cl H 678 CH₂F Cl H 679 CHF₂ Cl H 680 CF₃ Cl H 681 CH₂CF₃ Cl H 682 CH₂OCH₃ Cl H 683 CH₂OCH₂CH₃ Cl H 684 CH₂NH₂ Cl H 685 OCH₃ Cl H 686 OC₂H₅ Cl H 687 O-n-C₃H₇ Cl H 688 O-i-C₃H₇ Cl H 689 O-n-C₄H₉ Cl H 690 O-s-C₄H₉ Cl H 691 O-i-C₄H₉ Cl H 692 O-t-C₄H₉ Cl H 693 OCHF₂ Cl H 694 OCF₃ Cl H 695 OCH₂CF₃ Cl H 696 OCH₂OCH₃ Cl H 697 SCH₃ Cl H 698 SC₂H₅ Cl H 699 S-n-C₃H₇ Cl H 700 S-i-C₃H₇ Cl H 701 S-n-C₄H₉ Cl H 702 S-s-C₄H₉ Cl H 703 S-i-C₄H₉ Cl H 704 S-t-C₄H₉ Cl H 705 SCHF₂ Cl H 706 SCF₃ Cl H 707 SCH₂CF₃ Cl H 708 SCH₂OCH₃ Cl H 709 NHCH₃ Cl H 710 NHC₂H₅ Cl H 711 NHPh Cl H 712 N(CH₃)₂ Cl H 713 N(CH₂CH₃)₂ Cl H 714 N(phenyl)₂ Cl H 715 (CH₂)₂COCH₃ Cl H 716 phenyl Cl H 717 2-F-phenyl Cl H 718 3-F-phenyl Cl H 719 4-F-phenyl Cl H 720 2-Cl-phenyl Cl H 721 3-Cl-phenyl Cl H 722 4-Cl-phenyl Cl H 723 2-OH-phenyl Cl H 724 3-OH-phenyl Cl H 725 4-OH-phenyl Cl H 726 2-OCH₃-phenyl Cl H 727 3-OCH₃-phenyl Cl H 728 4-OCH₃-phenyl Cl H 729 2-OCF₃-phenyl Cl H 730 3-OCF₃-phenyl Cl H 731 4-OCF₃-phenyl Cl H 732 2-OCHF₂-phenyl Cl H 733 3-OCHF₂-phenyl Cl H 734 4-OCHF₂-phenyl Cl H 735 2-CF₃-phenyl Cl H 736 3-CF₃-phenyl Cl H 737 4-CF₃-phenyl Cl H 738 2-CH₃-phenyl Cl H 739 3-CH₃-phenyl Cl H 740 4-CH₃-phenyl Cl H 741 2-NO₂-phenyl Cl H 742 3-NO₂-phenyl Cl H 743 4-NO₂-phenyl Cl H 744 2-pyridyl Cl H 745 3-pyridyl Cl H 746 4-pyridyl Cl H 747 3′-CH₃-2-pyridyl Cl H 748 4′-CH₃-2-pyridyl Cl H 749 5′-CH₃-2-pyridyl Cl H 750 6′-CH₃-2-pyridyl Cl H 751 2′-CH₃-3-pyridyl Cl H 752 4′-CH₃-3-pyridyl Cl H 753 5′-CH₃-3-pyridyl Cl H 754 6′-CH₃-3-pyridyl Cl H 755 2′-CH₃-4-pyridyl Cl H 756 3′-CH₃-4-pyridyl Cl H 757 3′-Cl-2-pyridyl Cl H 758 4′-Cl-2-pyridyl Cl H 759 5′-Cl-2-pyridyl Cl H 760 6′-Cl-2-pyridyl Cl H 761 2′-Cl-3-pyridyl Cl H 762 4′-Cl-3-pyridyl Cl H 763 5′-Cl-3-pyridyl Cl H 764 6′-Cl-3-pyridyl Cl H 765 2′-Cl-4-pyridyl Cl H 766 3′-Cl-4-pyridyl Cl H 767 cyclohexylamino Cl H 768 cyclopentylamino Cl H 769 morpholino Cl H 770 CO₂H Cl H 771 CO₂CH₃ Cl H 772 CO₂C₂H₅ Cl H 773 CO₂-n-C₃H₇ Cl H 774 CO₂-i-C₃H₇ Cl H 775 CO₂-n-C₄H₉ Cl H 776 CO₂-s-C₄H₉ Cl H 777 CO₂-i-C₄H₉ Cl H 778 CO₂-t-C₄H₉ Cl H 779 CO₂-phenyl Cl H 780 CO₂-3-pyridyl Cl H 781 CONHCH₃ Cl H 782 CONHC₂H₅ Cl H 783 CONH-phenyl Cl H 784 CON(CH₃)₂ Cl H 785 CON(CH₂CH₃)₂ Cl H 786 CON(phenyl)₂ Cl H 787 2-fluorophenoxy CH₃ CH₃ 788 2-fluorophenoxy OCH₃ CH₃ 789 2-fluorophenoxy Cl CH₃ 790 2-fluorophenoxy CH₃ H 791 2-fluorophenoxy OCH₃ H 792 2-fluorophenoxy Cl H 793 phenoxy CH₃ CH₃ 794 phenoxy OCH₃ CH₃ 795 phenoxy Cl CH₃ 796 phenoxy CH₃ H 797 phenoxy OCH₃ H 798 phenoxy Cl H 799 2-methoxyphenoxy CH₃ CH₃ 800 2-methoxyphenoxy OCH₃ CH₃ 801 2-methoxyphenoxy Cl CH₃ 802 2-methoxyphenoxy CH₃ H 803 2-methoxyphenoxy OCH₃ H 804 2-methoxyphenoxy Cl H 805 cyclopropyl CH₃ CH₃ 806 cyclopropyl OCH₃ CH₃ 807 cyclopropyl Cl CH₃ 808 cyclopropyl CH₃ H 809 cyclopropyl OCH₃ H 810 cyclopropyl Cl H

The meanings of the abbreviations given here and below are, for example:

2-F-phenyl=2-fluorophenyl

2-Cl-phenyl=2-chlorophenyl

2-OH-phenyl=2-hydroxyphenyl

2-OCH₃-phenyl=2-methoxyphenyl

2-OCF₃-phenyl=2-trifluoromethoxyphenyl

2-OCHF₂-phenyl=2-difluoromethoxyphenyl

2-NO₂-phenyl=2-nitrophenyl

3′-CH₃-2-pyridyl=3′-methylpyridin-2-yl

Examples of particularly preferred benzothiazol-5-ylcarbonyl derivatives of pyrazoles according to the invention (compounds I-1=compounds I where X=C—R³ and Y=S) are the compounds listed in Tables 2 to 20.

TABLE 2 Compounds I-1a.1 to I-1a.810

I-1a

Compounds of the formula I-1a where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 3 Compounds I-1b.1 to I-1b.810

I-1b

Compounds of the formula I-1b where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 4 Compounds I-1c.1 to I-1c.810

I-1c

Compounds of the formula I-1c where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 5 Compounds I-1d.1 to I-1d.810

I-1d

Compounds of the formula I-1d where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 6 Compounds I-1e.1 to I-1e.810

I-1e

Compounds of the formula I-1e where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 7 Compounds I-1f.1 to I-1f.810

I-1f

Compounds of the formula I-1f where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 8 Compounds I-1g.1 to I-1g.810

I-1g

Compounds of the formula I-1g where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 9 Compounds I-1h.1 to I-1h.810

I-1h

Compounds of the formula I-1h where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 10 Compounds I-1i.1 to I-1i.810

I-1i

Compounds of the formula I-1i where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 11 Compounds I-1k.1 to I-1k.810

I-1k

Compounds of the formula I-1k where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 12 Compounds I-1l.1 to I-1l.810

I-1l

Compounds of the formula I-1l where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 13 Compounds I-1m.1 to I-1m.810

I-1m

Compounds of the formula I-1m where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 14 Compounds I-1n.1 to I-1n.810

I-1n

Compounds of the formula I-1n where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 15 Compounds I-1o.1 to I-1o.810

I-1o

Compounds of the formula I-1o where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 16 Compounds I-1p.1 to I-1p.810

I-1p

Compounds of the formula I-1p where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 17 Compounds I-1q.1 to I-1q.810

I-1q

Compounds of the formula I-1q where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 18 Compounds I-1r.1 to I-1r.810

I-1r

Compounds of the formula I-1r where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 19 Compounds I-1s.1 to I-1s.810

I-1s

Compounds of the formula I-1s where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 20 Compounds I-1t.1 to I-1t.810

I-1t

Compounds of the formula I-1t where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 20a Compounds I-1u.1 to I-1u.810

I-1u

Compounds of the formula I-1u where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 20b Compounds I-1v.1 to I-1v.810

I-1v

Compounds of the formula I-1v where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 20c Compounds I-1w.1 to I-1w.810

I-1w

Compounds of the formula I-1w where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

Examples of particularly preferred pyrazolyl derivatives according to the invention are the benzothiazole S-dioxide compounds 1-1′a.1 to 1-1′a.810, 1-1′b.1 to 1-1′b.810, . . . 1-1′w.1 to 1-1′w.810 (compounds I-1′, =compounds I where X=C—R₃ and Y=SO₂). They differ from the benzothiazole compounds 1-1a.1 to 1-1a.810, 1-1b.1 to 1-1b.810, . . . 1-1w.1 to 1-1w.810 listed in Tables 1 to 20 in that the heterocyclic sulfur atom is present as an SO₂ group.

Examples of particularly preferred pyrazolyl derivatives of benzoxazole 5-carbonyl compounds according to the invention (compounds I-2=compounds I where X=C—R³ and Y=O) are the compounds mentioned in Tables 21 to 39.

TABLE 21 Compounds I-2a.1 to I-2a.810

I-2a

Compounds of the formula I-2a where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 22 Compounds I-2b.1 to I-2b.810

I-2b

Compounds of the formula I-2b where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 23 Compounds I-2c.1 to I-2c.810

I-2c

Compounds of the formula I-2c where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 24 Compounds I-2d.1 to I-2d.810

I-2d

Compounds of the formula I-2d where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 25 Compounds I-2e.1 to I-2e.810

I-2e

Compounds of the formula I-2e where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 26 Compounds I-2f.1 to I-2f.810

I-2f

Compounds of the formula I-2f where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 27 Compounds I-2g.1 to I-2g.810

I-2g

Compounds of the formula I-2g where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 28 Compounds I-2h.1 to I-2h.810

I-2h

Compounds of the formula I-2h where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 29 Compounds I-2i.1 to I-2i.810

I-2i

Compounds of the formula I-2i where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 30 Compounds I-2k.1 to I-2k.810

I-2k

Compounds of the formula I-2k where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 31 Compounds I-2l.1 to I-2l.810

I-2l

Compounds of the formula I-2l where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 32 Compounds I-2m.1 to I-2m.810

I-2m

Compounds of the formula I-2m where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 33 Compounds I-2n.1 to I-2n.810

I-2n

Compounds of the formula I-2n where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 34 Compounds I-2o.1 to I-2o.810

I-2o

Compounds of the formula I-2o where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 35 Compounds I-2p.1 to I-2p.810

I-2p

Compounds of the formula I-2p where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 36 Compounds I-2q.1 to I-2q.810

I-2q

Compounds of the formula I-2q where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 37 Compounds I-2r.1 to I-2r.810

I-2r

Compounds of the formula I-2r where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 38 Compounds I-2s.1 to I-2s.810

I-2s

Compounds of the formula I-2s where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 39 Compounds I-2t.1 to I-2t.810

I-2t

Compounds of the formula I-2t where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 39a Compounds I-2u.1 to I-2u.810

I-2u

Compounds of the formula I-2u where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 39b Compounds I-2v.1 to I-2v.810

I-2v

Compounds of the formula I-2v where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

TABLE 39c Compounds I-2w.1 to I-2w.810

I-2w

Compounds of the formula I-2w where the substituents R¹, R² and R³ for each individual compound correspond in each case to one row of Table A.

Particularly preferred combinations of R¹, R², R³ and R⁴ for pyrazole derivatives of the formula I according to the invention which are derived from benzimidazole-5-carboxylic acids are listed in Table B below.

TABLE B R³ R¹ R² R⁴ 1 CH₃ CH₃ CH₃ H 2 C₂H₅ CH₃ CH₃ H 3 n-C₃H₇ CH₃ CH₃ H 4 i-C₃H₇ CH₃ CH₃ H 5 n-C₄C₉ CH₃ CH₃ H 6 s-C₄C₉ CH₃ CH₃ H 7 i-C₄C₉ CH₃ CH₃ H 8 t-C₄C₉ CH₃ CH₃ H 9 CH₂Cl CH₃ CH₃ H 10 CHCl₂ CH₃ CH₃ H 11 CCl₃ CH₃ CH₃ H 12 CH₂F CH₃ CH₃ H 13 CHF₂ CH₃ CH₃ H 14 CF₃ CH₃ CH₃ H 15 CH₂CF₃ CH₃ CH₃ H 16 CH₂OCH₃ CH₃ CH₃ H 17 CH₂OCH₂CH₃ CH₃ CH₃ H 18 CH₂NH₂ CH₃ CH₃ H 19 (CH₂)₂COCH₃ CH₃ CH₃ H 20 phenyl CH₃ CH₃ H 21 2-F-phenyl CH₃ CH₃ H 22 3-F-phenyl CH₃ CH₃ H 23 4-F-phenyl CH₃ CH₃ H 24 2-Cl-phenyl CH₃ CH₃ H 25 3-Cl-phenyl CH₃ CH₃ H 26 4-Cl-phenyl CH₃ CH₃ H 27 2-OH-phenyl CH₃ CH₃ H 28 3-OH-phenyl CH₃ CH₃ H 29 4-OH-phenyl CH₃ CH₃ H 30 2-OCH₃-phenyl CH₃ CH₃ H 31 3-OCH₃-phenyl CH₃ CH₃ H 32 4-OCH₃-phenyl CH₃ CH₃ H 33 2-OCF₃-phenyl CH₃ CH₃ H 34 3-OCF₃-phenyl CH₃ CH₃ H 35 4-OCF₃-phenyl CH₃ CH₃ H 36 2-OCHF₂-phenyl CH₃ CH₃ H 37 3-OCHF₂-phenyl CH₃ CH₃ H 38 4-OCHF₂-phenyl CH₃ CH₃ H 39 2-CF₃-phenyl CH₃ CH₃ H 40 3-CF₃-phenyl CH₃ CH₃ H 41 4-CF₃-phenyl CH₃ CH₃ H 42 2-CH₃-phenyl CH₃ CH₃ H 43 3-CH₃-phenyl CH₃ CH₃ H 44 4-CH₃-phenyl CH₃ CH₃ H 45 2-NO₂-phenyl CH₃ CH₃ H 46 3-NO₂-phenyl CH₃ CH₃ H 47 4-NO₂-phenyl CH₃ CH₃ H 48 2-pyridyl CH₃ CH₃ H 49 3-pyridyl CH₃ CH₃ H 50 4-pyridyl CH₃ CH₃ H 51 cyclohexylamino CH₃ CH₃ H 52 cyclopentylamino CH₃ CH₃ H 53 H OCH₃ CH₃ H 54 CH₃ OCH₃ CH₃ H 55 C₂H₅ OCH₃ CH₃ H 56 n-C₃H₇ OCH₃ CH₃ H 57 i-C₃H₇ OCH₃ CH₃ H 58 n-C₄C₉ OCH₃ CH₃ H 59 s-C₄C₉ OCH₃ CH₃ H 60 i-C₄C₉ OCH₃ CH₃ H 61 t-C₄C₉ OCH₃ CH₃ H 62 CH₂Cl OCH₃ CH₃ H 63 CHCl₂ OCH₃ CH₃ H 64 CCl₃ OCH₃ CH₃ H 65 CH₂F OCH₃ CH₃ H 66 CHF₂ OCH₃ CH₃ H 67 CF₃ OCH₃ CH₃ H 68 CH₂CF₃ OCH₃ CH₃ H 69 CH₂OCH₃ OCH₃ CH₃ H 70 CH₂OCH₂CH₃ OCH₃ CH₃ H 71 CH₂NH₂ OCH₃ CH₃ H 72 (CH₂)₂COCH₃ OCH₃ CH₃ H 73 phenyl OCH₃ CH₃ H 74 2-F-phenyl OCH₃ CH₃ H 75 3-F-phenyl OCH₃ CH₃ H 76 4-F-phenyl OCH₃ CH₃ H 77 2-Cl-phenyl OCH₃ CH₃ H 78 3-Cl-phenyl OCH₃ CH₃ H 79 4-Cl-phenyl OCH₃ CH₃ H 80 2-OH-phenyl OCH₃ CH₃ H 81 3-OH-phenyl OCH₃ CH₃ H 82 4-OH-phenyl OCH₃ CH₃ H 83 2-OCH₃-phenyl OCH₃ CH₃ H 84 3-OCH₃-phenyl OCH₃ CH₃ H 85 4-OCH₃-phenyl OCH₃ CH₃ H 86 2-OCF₃-phenyl OCH₃ CH₃ H 87 3-OCF₃-phenyl OCH₃ CH₃ H 88 4-OCF₃-phenyl OCH₃ CH₃ H 89 2-OCHF₂-phenyl OCH₃ CH₃ H 90 3-OCHF₂-phenyl OCH₃ CH₃ H 91 4-OCHF₂-phenyl OCH₃ CH₃ H 92 2-CF₃-phenyl OCH₃ CH₃ H 93 3-CF₃-phenyl OCH₃ CH₃ H 94 4-CF₃-phenyl OCH₃ CH₃ H 25 2-CH₃-phenyl OCH₃ CH₃ H 96 3-CH₃-phenyl OCH₃ CH₃ H 97 4-CH₃-phenyl OCH₃ CH₃ H 98 2-NO₂-phenyl OCH₃ CH₃ H 99 3-NO₂-phenyl OCH₃ CH₃ H 100 4-NO₂-phenyl OCH₃ CH₃ H 101 2-pyridyl OCH₃ CH₃ H 102 3-pyridyl OCH₃ CH₃ H 103 4-pyridyl OCH₃ CH₃ H 104 cyclohexylamino OCH₃ CH₃ H 105 cyclopentylamino OCH₃ CH₃ H 106 H Cl CH₃ H 107 CH₃ Cl CH₃ H 108 C₂H₅ Cl CH₃ H 109 n-C₃H₇ Cl CH₃ H 110 i-C₃H₇ Cl CH₃ H 111 n-C₄C₉ Cl CH₃ H 112 s-C₄C₉ Cl CH₃ H 113 i-C₄C₉ Cl CH₃ H 114 t-C₄C₉ Cl CH₃ H 115 CH₂Cl Cl CH₃ H 116 CHCl₂ Cl CH₃ H 117 CCl₃ Cl CH₃ H 118 CH₂F Cl CH₃ H 119 CHF₂ Cl CH₃ H 120 CF₃ Cl CH₃ H 121 CH₂CF₃ Cl CH₃ H 122 CH₂OCH₃ Cl CH₃ H 123 CH₂OCH₂CH₃ Cl CH₃ H 124 CH₂NH₂ Cl CH₃ H 125 (CH₂)₂COCH₃ Cl CH₃ H 126 phenyl Cl CH₃ H 127 2-F-phenyl Cl CH₃ H 128 3-F-phenyl Cl CH₃ H 129 4-F-phenyl Cl CH₃ H 130 2-Cl-phenyl Cl CH₃ H 131 3-Cl-phenyl Cl CH₃ H 132 4-Cl-phenyl Cl CH₃ H 133 2-OH-phenyl Cl CH₃ H 134 3-OH-phenyl Cl CH₃ H 135 4-OH-phenyl Cl CH₃ H 136 2-OCH₃-phenyl Cl CH₃ H 137 3-OCH₃-phenyl Cl CH₃ H 138 4-OCH₃-phenyl Cl CH₃ H 139 2-OCF₃-phenyl Cl CH₃ H 140 3-OCF₃-phenyl Cl CH₃ H 141 4-OCF₃-phenyl Cl CH₃ H 142 2-OCHF₂-phenyl Cl CH₃ H 143 3-OCHF₂-phenyl Cl CH₃ H 144 4-OCHF₂-phenyl Cl CH₃ H 145 2-CF₃-phenyl Cl CH₃ H 146 3-CF₃-phenyl Cl CH₃ H 147 4-CF₃-phenyl Cl CH₃ H 148 2-CH₃-phenyl Cl CH₃ H 149 3-CH₃-phenyl Cl CH₃ H 150 4-CH₃-phenyl Cl CH₃ H 151 2-NO₂-phenyl Cl CH₃ H 152 3-NO₂-phenyl Cl CH₃ H 153 4-NO₂-phenyl Cl CH₃ H 154 2-pyridyl Cl CH₃ H 155 3-pyridyl Cl CH₃ H 156 4-pyridyl Cl CH₃ H 157 cyclohexylamino Cl CH₃ H 158 cyclopentylamino Cl CH₃ H 159 CH₃ CH₃ H H 160 C₂H₅ CH₃ H H 161 n-C₃H₇ CH₃ H H 162 i-C₃H₇ CH₃ H H 163 n-C₄C₉ CH₃ H H 164 s-C₄C₉ CH₃ H H 165 i-C₄C₉ CH₃ H H 166 t-C₄C₉ CH₃ H H 167 CH₂Cl CH₃ H H 168 CHCl₂ CH₃ H H 169 CCl₃ CH₃ H H 170 CH₂F CH₃ H H 171 CHF₂ CH₃ H H 172 CF₃ CH₃ H H 173 CH₂CF₃ CH₃ H H 174 CH₂OCH₃ CH₃ H H 175 CH₂OCH₂CH₃ CH₃ H H 176 CH₂NH₂ CH₃ H H 177 (CH₂)₂COCH₃ CH₃ H H 178 phenyl CH₃ H H 179 2-F-phenyl CH₃ H H 180 3-F-phenyl CH₃ H H 181 4-F-phenyl CH₃ H H 182 2-Cl-phenyl CH₃ H H 183 3-Cl-phenyl CH₃ H H 184 4-Cl-phenyl CH₃ H H 185 2-OH-phenyl CH₃ H H 186 3-OH-phenyl CH₃ H H 187 4-OH-phenyl CH₃ H H 188 2-OCH₃-phenyl CH₃ H H 189 3-OCH₃-phenyl CH₃ H H 190 4-OCH₃-phenyl CH₃ H H 191 2-OCF₃-phenyl CH₃ H H 192 3-OCF₃-phenyl CH₃ H H 193 4-OCF₃-phenyl CH₃ H H 194 2-OCHF₂-phenyl CH₃ H H 195 3-OCHF₂-phenyl CH₃ H H 196 4-OCHF₂-phenyl CH₃ H H 197 2-CF₃-phenyl CH₃ H H 198 3-CF₃-phenyl CH₃ H H 199 4-CF₃-phenyl CH₃ H H 200 2-CH₃-phenyl CH₃ H H 201 3-CH₃-phenyl CH₃ H H 202 4-CH₃-phenyl CH₃ H H 203 2-NO₂-phenyl CH₃ H H 204 3-NO₂-phenyl CH₃ H H 205 4-NO₂-phenyl CH₃ H H 206 2-pyridyl CH₃ H H 207 3-pyridyl CH₃ H H 208 4-pyridyl CH₃ H H 209 cyclohexylamino CH₃ H H 210 cyclopentylamino CH₃ H H 211 H OCH₃ H H 212 CH₃ OCH₃ H H 213 C₂H₅ OCH₃ H H 214 n-C₃H₇ OCH₃ H H 215 i-C₃H₇ OCH₃ H H 216 n-C₄C₉ OCH₃ H H 217 s-C₄C₉ OCH₃ H H 218 i-C₄C₉ OCH₃ H H 219 t-C₄C₉ OCH₃ H H 220 CH₂Cl OCH₃ H H 221 CHCl₂ OCH₃ H H 222 CCl₃ OCH₃ H H 223 CH₂F OCH₃ H H 224 CHF₂ OCH₃ H H 225 CF₃ OCH₃ H H 226 CH₂CF₃ OCH₃ H H 227 CH₂OCH₃ OCH₃ H H 228 CH₂OCH₂CH₃ OCH₃ H H 229 CH₂NH₂ OCH₃ H H 230 (CH₂)₂COCH₃ OCH₃ H H 231 phenyl OCH₃ H H 232 2-F-phenyl OCH₃ H H 233 3-F-phenyl OCH₃ H H 234 4-F-phenyl OCH₃ H H 235 2-Cl-phenyl OCH₃ H H 236 3-Cl-phenyl OCH₃ H H 237 4-Cl-phenyl OCH₃ H H 238 2-OH-phenyl OCH₃ H H 239 3-OH-phenyl OCH₃ H H 240 4-OH-phenyl OCH₃ H H 241 2-OCH₃-phenyl OCH₃ H H 242 3-OCH₃-phenyl OCH₃ H H 243 4-OCH₃-phenyl OCH₃ H H 244 2-OCF₃-phenyl OCH₃ H H 245 3-OCF₃-phenyl OCH₃ H H 246 4-OCF₃-phenyl OCH₃ H H 247 2-OCHF₂-phenyl OCH₃ H H 248 3-OCHF₂-phenyl OCH₃ H H 249 4-OCHF₂-phenyl OCH₃ H H 250 2-CF₃-phenyl OCH₃ H H 251 3-CF₃-phenyl OCH₃ H H 252 4-CF₃-phenyl OCH₃ H H 253 2-CH₃-phenyl OCH₃ H H 254 3-CH₃-phenyl OCH₃ H H 255 4-CH₃-phenyl OCH₃ H H 256 2-NO₂-phenyl OCH₃ H H 257 3-NO₂-phenyl OCH₃ H H 258 4-NO₂-phenyl OCH₃ H H 259 2-pyridyl OCH₃ H H 260 3-pyridyl OCH₃ H H 261 4-pyridyl OCH₃ H H 262 cyclohexylamino OCH₃ H H 263 cyclopentylamino OCH₃ H H 264 H Cl H H 265 CH₃ Cl H H 266 C₂H₅ Cl H H 267 n-C₃H₇ Cl H H 268 i-C₃H₇ Cl H H 269 n-C₄C₉ Cl H H 270 s-C₄C₉ Cl H H 271 i-C₄C₉ Cl H H 272 t-C₄C₉ Cl H H 273 CH₂Cl Cl H H 274 CHCl₂ Cl H H 275 CCl₃ Cl H H 276 CH₂F Cl H H 277 CHF₂ Cl H H 278 CF₃ Cl H H 279 CH₂CF₃ Cl H H 280 CH₂OCH₃ Cl H H 281 CH₂OCH₂CH₃ Cl H H 282 CH₂NH₂ Cl H H 283 (CH₂)₂COCH₃ Cl H H 284 phenyl Cl H H 285 2-F-phenyl Cl H H 286 3-F-phenyl Cl H H 287 4-F-phenyl Cl H H 288 2-Cl-phenyl Cl H H 289 3-Cl-phenyl Cl H H 290 4-Cl-phenyl Cl H H 291 2-OH-phenyl Cl H H 292 3-OH-phenyl Cl H H 293 4-OH-phenyl Cl H H 294 2-OCH₃-phenyl Cl H H 295 3-OCH₃-phenyl Cl H H 296 4-OCH₃-phenyl Cl H H 297 2-OCF₃-phenyl Cl H H 298 3-OCF₃-phenyl Cl H H 299 4-OCF₃-phenyl Cl H H 300 2-OCHF₂-phenyl Cl H H 301 3-OCHF₂-phenyl Cl H H 302 4-OCHF₂-phenyl Cl H H 303 2-CF₃-phenyl Cl H H 304 3-CF₃-phenyl Cl H H 305 4-CF₃-phenyl Cl H H 306 2-CH₃-phenyl Cl H H 307 3-CH₃-phenyl Cl H H 308 4-CH₃-phenyl Cl H H 309 2-NO₂-phenyl Cl H H 310 3-NO₂-phenyl Cl H H 311 4-NO₂-phenyl Cl H H 312 2-pyridyl Cl H H 313 3-pyridyl Cl H H 314 4-pyridyl Cl H H 315 cyclohexylamino Cl H H 316 cyclopentylamino Cl H H 317 CH₃ CH₃ CH₃ CH₃ 318 C₂H₅ CH₃ CH₃ CH₃ 319 n-C₃H₇ CH₃ CH₃ CH₃ 320 i-C₃H₇ CH₃ CH₃ CH₃ 321 n-C₄C₉ CH₃ CH₃ CH₃ 322 s-C₄C₉ CH₃ CH₃ CH₃ 323 i-C₄C₉ CH₃ CH₃ CH₃ 324 t-C₄C₉ CH₃ CH₃ CH₃ 325 CH₂Cl CH₃ CH₃ CH₃ 326 CHCl₂ CH₃ CH₃ CH₃ 327 CCl₃ CH₃ CH₃ CH₃ 328 CH₂F CH₃ CH₃ CH₃ 329 CHF₂ CH₃ CH₃ CH₃ 330 CF₃ CH₃ CH₃ CH₃ 331 CH₂CF₃ CH₃ CH₃ CH₃ 332 CH₂OCH₃ CH₃ CH₃ CH₃ 333 CH₂OCH₂CH₃ CH₃ CH₃ CH₃ 334 CH₂NH₂ CH₃ CH₃ CH₃ 335 (CH₂)₂COCH₃ CH₃ CH₃ CH₃ 336 phenyl CH₃ CH₃ CH₃ 337 2-F-phenyl CH₃ CH₃ CH₃ 338 3-F-phenyl CH₃ CH₃ CH₃ 339 4-F-phenyl CH₃ CH₃ CH₃ 340 2-Cl-phenyl CH₃ CH₃ CH₃ 341 3-Cl-phenyl CH₃ CH₃ CH₃ 342 4-Cl-phenyl CH₃ CH₃ CH₃ 343 2-OH-phenyl CH₃ CH₃ CH₃ 344 3-OH-phenyl CH₃ CH₃ CH₃ 345 4-OH-phenyl CH₃ CH₃ CH₃ 346 2-OCH₃-phenyl CH₃ CH₃ CH₃ 347 3-OCH₃-phenyl CH₃ CH₃ CH₃ 348 4-OCH₃-phenyl CH₃ CH₃ CH₃ 349 2-OCF₃-phenyl CH₃ CH₃ CH₃ 350 3-OCF₃-phenyl CH₃ CH₃ CH₃ 351 4-OCF₃-phenyl CH₃ CH₃ CH₃ 352 2-OCHF₂-phenyl CH₃ CH₃ CH₃ 353 3-OCHF₂-phenyl CH₃ CH₃ CH₃ 354 4-OCHF₂-phenyl CH₃ CH₃ CH₃ 355 2-CF₃-phenyl CH₃ CH₃ CH₃ 356 3-CF₃-phenyl CH₃ CH₃ CH₃ 357 4-CF₃-phenyl CH₃ CH₃ CH₃ 358 2-CH₃-phenyl CH₃ CH₃ CH₃ 359 3-CH₃-phenyl CH₃ CH₃ CH₃ 360 4-CH₃-phenyl CH₃ CH₃ CH₃ 361 2-NO₂-phenyl CH₃ CH₃ CH₃ 362 3-NO₂-phenyl CH₃ CH₃ CH₃ 363 4-NO₂-phenyl CH₃ CH₃ CH₃ 364 2-pyridyl CH₃ CH₃ CH₃ 365 3-pyridyl CH₃ CH₃ CH₃ 366 4-pyridyl CH₃ CH₃ CH₃ 367 cyclohexylamino CH₃ CH₃ CH₃ 368 cyclopentylamino CH₃ CH₃ CH₃ 369 H OCH₃ CH₃ CH₃ 370 CH₃ OCH₃ CH₃ CH₃ 371 C₂H₅ OCH₃ CH₃ CH₃ 372 n-C₃H₇ OCH₃ CH₃ CH₃ 373 i-C₃H₇ OCH₃ CH₃ CH₃ 374 n-C₄C₉ OCH₃ CH₃ CH₃ 375 s-C₄C₉ OCH₃ CH₃ CH₃ 376 i-C₄C₉ OCH₃ CH₃ CH₃ 377 t-C₄C₉ OCH₃ CH₃ CH₃ 378 CH₂Cl OCH₃ CH₃ CH₃ 379 CHCl₂ OCH₃ CH₃ CH₃ 380 CCl₃ OCH₃ CH₃ CH₃ 381 CH₂F OCH₃ CH₃ CH₃ 382 CHF₂ OCH₃ CH₃ CH₃ 383 CF₃ OCH₃ CH₃ CH₃ 384 CH₂CF₃ OCH₃ CH₃ CH₃ 385 CH₂OCH₃ OCH₃ CH₃ CH₃ 386 CH₂OCH₂CH₃ OCH₃ CH₃ CH₃ 387 CH₂NH₂ OCH₃ CH₃ CH₃ 388 (CH₂)₂COCH₃ OCH₃ CH₃ CH₃ 389 phenyl OCH₃ CH₃ CH₃ 390 2-F-phenyl OCH₃ CH₃ CH₃ 391 3-F-phenyl OCH₃ CH₃ CH₃ 392 4-F-phenyl OCH₃ CH₃ CH₃ 393 2-Cl-phenyl OCH₃ CH₃ CH₃ 394 3-Cl-phenyl OCH₃ CH₃ CH₃ 395 4-Cl-phenyl OCH₃ CH₃ CH₃ 396 2-OH-phenyl OCH₃ CH₃ CH₃ 397 3-OH-phenyl OCH₃ CH₃ CH₃ 398 4-OH-phenyl OCH₃ CH₃ CH₃ 399 2-OCH₃-phenyl OCH₃ CH₃ CH₃ 400 3-OCH₃-phenyl OCH₃ CH₃ CH₃ 401 4-OCH₃-phenyl OCH₃ CH₃ CH₃ 402 2-OCF₃-phenyl OCH₃ CH₃ CH₃ 403 3-OCF₃-phenyl OCH₃ CH₃ CH₃ 404 4-OCF₃-phenyl OCH₃ CH₃ CH₃ 405 2-OCHF₂-phenyl OCH₃ CH₃ CH₃ 406 3-OCHF₂-phenyl OCH₃ CH₃ CH₃ 407 4-OCHF₂-phenyl OCH₃ CH₃ CH₃ 408 2-CF₃-phenyl OCH₃ CH₃ CH₃ 409 3-CF₃-phenyl OCH₃ CH₃ CH₃ 410 4-CF₃-phenyl OCH₃ CH₃ CH₃ 411 2-CH₃-phenyl OCH₃ CH₃ CH₃ 412 3-CH₃-phenyl OCH₃ CH₃ CH₃ 413 4-CH₃-phenyl OCH₃ CH₃ CH₃ 414 2-NO₂-phenyl OCH₃ CH₃ CH₃ 415 3-NO₂-phenyl OCH₃ CH₃ CH₃ 416 4-NO₂-phenyl OCH₃ CH₃ CH₃ 417 2-pyridyl OCH₃ CH₃ CH₃ 418 3-pyridyl OCH₃ CH₃ CH₃ 419 4-pyridyl OCH₃ CH₃ CH₃ 420 cyclohexylamino OCH₃ CH₃ CH₃ 421 cyclopentylamino OCH₃ CH₃ CH₃ 422 H Cl CH₃ CH₃ 423 CH₃ Cl CH₃ CH₃ 424 C₂H₅ Cl CH₃ CH₃ 425 n-C₃H₇ Cl CH₃ CH₃ 426 i-C₃H₇ Cl CH₃ CH₃ 427 n-C₄C₉ Cl CH₃ CH₃ 428 s-C₄C₉ Cl CH₃ CH₃ 429 i-C₄C₉ Cl CH₃ CH₃ 430 t-C₄C₉ Cl CH₃ CH₃ 431 CH₂Cl Cl CH₃ CH₃ 432 CHCl₂ Cl CH₃ CH₃ 433 CCl₃ Cl CH₃ CH₃ 434 CH₂F Cl CH₃ CH₃ 435 CHF₂ Cl CH₃ CH₃ 436 CF₃ Cl CH₃ CH₃ 437 CH₂CF₃ Cl CH₃ CH₃ 438 CH₂OCH₃ Cl CH₃ CH₃ 439 CH₂OCH₂CH₃ Cl CH₃ CH₃ 440 CH₂NH₂ Cl CH₃ CH₃ 441 (CH₂)₂COCH₃ Cl CH₃ CH₃ 442 phenyl Cl CH₃ CH₃ 443 2-F-phenyl Cl CH₃ CH₃ 444 3-F-phenyl Cl CH₃ CH₃ 445 4-F-phenyl Cl CH₃ CH₃ 446 2-Cl-phenyl Cl CH₃ CH₃ 447 3-Cl-phenyl Cl CH₃ CH₃ 448 4-Cl-phenyl Cl CH₃ CH₃ 449 2-OH-phenyl Cl CH₃ CH₃ 450 3-OH-phenyl Cl CH₃ CH₃ 451 4-OH-phenyl Cl CH₃ CH₃ 452 2-OCH₃-phenyl Cl CH₃ CH₃ 453 3-OCH₃-phenyl Cl CH₃ CH₃ 454 4-OCH₃-phenyl Cl CH₃ CH₃ 455 2-OCF₃-phenyl Cl CH₃ CH₃ 456 3-OCF₃-phenyl Cl CH₃ CH₃ 457 4-OCF₃-phenyl Cl CH₃ CH₃ 458 2-OCHF₂-phenyl Cl CH₃ CH₃ 459 3-OCHF₂-phenyl Cl CH₃ CH₃ 460 4-OCHF₂-phenyl Cl CH₃ CH₃ 461 2-CF₃-phenyl Cl CH₃ CH₃ 462 3-CF₃-phenyl Cl CH₃ CH₃ 463 4-CF₃-phenyl Cl CH₃ CH₃ 464 2-CH₃-phenyl Cl CH₃ CH₃ 465 3-CH₃-phenyl Cl CH₃ CH₃ 466 4-CH₃-phenyl Cl CH₃ CH₃ 467 2-NO₂-phenyl Cl CH₃ CH₃ 468 3-NO₂-phenyl Cl CH₃ CH₃ 469 4-NO₂-phenyl Cl CH₃ CH₃ 470 2-pyridyl Cl CH₃ CH₃ 471 3-pyridyl Cl CH₃ CH₃ 472 4-pyridyl Cl CH₃ CH₃ 473 cyclohexylamino Cl CH₃ CH₃ 474 cyclopentylamino Cl CH₃ CH₃ 475 CH₃ CH₃ H CH₃ 476 C₂H₅ CH₃ H CH₃ 477 n-C₃H₇ CH₃ H CH₃ 478 i-C₃H₇ CH₃ H CH₃ 479 n-C₄C₉ CH₃ H CH₃ 480 s-C₄C₉ CH₃ H CH₃ 481 i-C₄C₉ CH₃ H CH₃ 482 t-C₄C₉ CH₃ H CH₃ 483 CH₂Cl CH₃ H CH₃ 484 CHCl₂ CH₃ H CH₃ 485 CCl₃ CH₃ H CH₃ 486 CH₂F CH₃ H CH₃ 487 CHF₂ CH₃ H CH₃ 488 CF₃ CH₃ H CH₃ 489 CH₂CF₃ CH₃ H CH₃ 490 CH₂OCH₃ CH₃ H CH₃ 491 CH₂OCH₂CH₃ CH₃ H CH₃ 492 CH₂NH₂ CH₃ H CH₃ 493 (CH₂)₂COCH₃ CH₃ H CH₃ 494 phenyl CH₃ H CH₃ 495 2-F-phenyl CH₃ H CH₃ 496 3-F-phenyl CH₃ H CH₃ 497 4-F-phenyl CH₃ H CH₃ 498 2-Cl-phenyl CH₃ H CH₃ 499 3-Cl-phenyl CH₃ H CH₃ 500 4-Cl-phenyl CH₃ H CH₃ 501 2-OH-phenyl CH₃ H CH₃ 502 3-OH-phenyl CH₃ H CH₃ 503 4-OH-phenyl CH₃ H CH₃ 504 2-OCH₃-phenyl CH₃ H CH₃ 505 3-OCH₃-phenyl CH₃ H CH₃ 506 4-OCH₃-phenyl CH₃ H CH₃ 507 2-OCF₃-phenyl CH₃ H CH₃ 508 3-OCF₃-phenyl CH₃ H CH₃ 509 4-OCF₃-phenyl CH₃ H CH₃ 510 2-OCHF₂-phenyl CH₃ H CH₃ 511 3-OCHF₂-phenyl CH₃ H CH₃ 512 4-OCHF₂-phenyl CH₃ H CH₃ 513 2-CF₃-phenyl CH₃ H CH₃ 514 3-CF₃-phenyl CH₃ H CH₃ 515 4-CF₃-phenyl CH₃ H CH₃ 516 2-CH₃-phenyl CH₃ H CH₃ 517 3-CH₃-phenyl CH₃ H CH₃ 518 4-CH₃-phenyl CH₃ H CH₃ 519 2-NO₂-phenyl CH₃ H CH₃ 520 3-NO₂-phenyl CH₃ H CH₃ 521 4-NO₂-phenyl CH₃ H CH₃ 522 2-pyridyl CH₃ H CH₃ 523 3-pyridyl CH₃ H CH₃ 524 4-pyridyl CH₃ H CH₃ 525 cyclohexylamino CH₃ H CH₃ 526 cyclopentylamino CH₃ H CH₃ 527 H OCH₃ H CH₃ 528 CH₃ OCH₃ H CH₃ 529 C₂H₅ OCH₃ H CH₃ 530 n-C₃H₇ OCH₃ H CH₃ 531 i-C₃H₇ OCH₃ H CH₃ 532 n-C₄C₉ OCH₃ H CH₃ 533 s-C₄C₉ OCH₃ H CH₃ 534 i-C₄C₉ OCH₃ H CH₃ 535 t-C₄C₉ OCH₃ H CH₃ 536 CH₂Cl OCH₃ H CH₃ 537 CHCl₂ OCH₃ H CH₃ 538 CCl₃ OCH₃ H CH₃ 539 CH₂F OCH₃ H CH₃ 540 CHF₂ OCH₃ H CH₃ 541 CF₃ OCH₃ H CH₃ 542 CH₂CF₃ OCH₃ H CH₃ 543 CH₂OCH₃ OCH₃ H CH₃ 544 CH₂OCH₂CH₃ OCH₃ H CH₃ 545 CH₂NH₂ OCH₃ H CH₃ 546 (CH₂)₂COCH₃ OCH₃ H CH₃ 547 phenyl OCH₃ H CH₃ 548 2-F-phenyl OCH₃ H CH₃ 549 3-F-phenyl OCH₃ H CH₃ 550 4-F-phenyl OCH₃ H CH₃ 551 2-Cl-phenyl OCH₃ H CH₃ 552 3-Cl-phenyl OCH₃ H CH₃ 553 4-Cl-phenyl OCH₃ H CH₃ 554 2-OH-phenyl OCH₃ H CH₃ 555 3-OH-phenyl OCH₃ H CH₃ 556 4-OH-phenyl OCH₃ H CH₃ 557 2-OCH₃-phenyl OCH₃ H CH₃ 558 3-OCH₃-phenyl OCH₃ H CH₃ 559 4-OCH₃-phenyl OCH₃ H CH₃ 560 2-OCF₃-phenyl OCH₃ H CH₃ 561 3-OCF₃-phenyl OCH₃ H CH₃ 562 4-OCF₃-phenyl OCH₃ H CH₃ 563 2-OCHF₂-phenyl OCH₃ H CH₃ 564 3-OCHF₂-phenyl OCH₃ H CH₃ 565 4-OCHF₂-phenyl OCH₃ H CH₃ 566 2-CF₃-phenyl OCH₃ H CH₃ 567 3-CF₃-phenyl OCH₃ H CH₃ 568 4-CF₃-phenyl OCH₃ H CH₃ 569 2-CH₃-phenyl OCH₃ H CH₃ 570 3-CH₃-phenyl OCH₃ H CH₃ 571 4-CH₃-phenyl OCH₃ H CH₃ 572 2-NO₂-phenyl OCH₃ H CH₃ 573 3-NO₂-phenyl OCH₃ H CH₃ 574 4-NO₂-phenyl OCH₃ H CH₃ 575 2-pyridyl OCH₃ H CH₃ 576 3-pyridyl OCH₃ H CH₃ 577 4-pyridyl OCH₃ H CH₃ 578 cyclohexylamino OCH₃ H CH₃ 579 cyclopentylamino OCH₃ H CH₃ 580 H Cl H CH₃ 581 CH₃ Cl H CH₃ 582 C₂H₅ Cl H CH₃ 583 n-C₃H₇ Cl H CH₃ 584 i-C₃H₇ Cl H CH₃ 585 n-C₄C₉ Cl H CH₃ 586 s-C₄C₉ Cl H CH₃ 587 i-C₄C₉ Cl H CH₃ 588 t-C₄C₉ Cl H CH₃ 589 CH₂Cl Cl H CH₃ 590 CHCl₂ Cl H CH₃ 591 CCl₃ Cl H CH₃ 592 CH₂F Cl H CH₃ 593 CHF₂ Cl H CH₃ 594 CF₃ Cl H CH₃ 595 CH₂CF₃ Cl H CH₃ 596 CH₂OCH₃ Cl H CH₃ 597 CH₂OCH₂CH₃ Cl H CH₃ 598 CH₂NH₂ Cl H CH₃ 599 (CH₂)₂COCH₃ Cl H CH₃ 600 phenyl Cl H CH₃ 701 2-F-phenyl Cl H CH₃ 702 3-F-phenyl Cl H CH₃ 703 4-F-phenyl Cl H CH₃ 704 2-Cl-phenyl Cl H CH₃ 705 3-Cl-phenyl Cl H CH₃ 706 4-Cl-phenyl Cl H CH₃ 707 2-OH-phenyl Cl H CH₃ 708 3-OH-phenyl Cl H CH₃ 709 4-OH-phenyl Cl H CH₃ 710 2-OCH₃-phenyl Cl H CH₃ 711 3-OCH₃-phenyl Cl H CH₃ 712 4-OCH₃-phenyl Cl H CH₃ 713 2-OCF₃-phenyl Cl H CH₃ 714 3-OCF₃-phenyl Cl H CH₃ 715 4-OCF₃-phenyl Cl H CH₃ 716 2-OCHF₂-phenyl Cl H CH₃ 717 3-OCHF₂-phenyl Cl H CH₃ 718 4-OCHF₂-phenyl Cl H CH₃ 719 2-CF₃-phenyl Cl H CH₃ 720 3-CF₃-phenyl Cl H CH₃ 721 4-CF₃-phenyl Cl H CH₃ 722 2-CH₃-phenyl Cl H CH₃ 723 3-CH₃-phenyl Cl H CH₃ 724 4-CH₃-phenyl Cl H CH₃ 725 2-NO₂-phenyl Cl H CH₃ 726 3-NO₂-phenyl Cl H CH₃ 727 4-NO₂-phenyl Cl H CH₃ 728 2-pyridyl Cl H CH₃ 729 3-pyridyl Cl H CH₃ 730 4-pyridyl Cl H CH₃ 731 cyclohexylamino Cl H CH₃ 732 cyclopentylamino Cl H CH₃ 733 CH₃ CH₃ CH₃ C₂H₅ 734 C₂H₅ CH₃ CH₃ C₂H₅ 735 n-C₃H₇ CH₃ CH₃ C₂H₅ 736 i-C₃H₇ CH₃ CH₃ C₂H₅ 737 n-C₄C₉ CH₃ CH₃ C₂H₅ 738 s-C₄C₉ CH₃ CH₃ C₂H₅ 739 i-C₄C₉ CH₃ CH₃ C₂H₅ 740 t-C₄C₉ CH₃ CH₃ C₂H₅ 741 CH₂Cl CH₃ CH₃ C₂H₅ 742 CHCl₂ CH₃ CH₃ C₂H₅ 743 CCl₃ CH₃ CH₃ C₂H₅ 744 CH₂F CH₃ CH₃ C₂H₅ 745 CHF₂ CH₃ CH₃ C₂H₅ 746 CF₃ CH₃ CH₃ C₂H₅ 747 CH₂CF₃ CH₃ CH₃ C₂H₅ 748 CH₂OCH₃ CH₃ CH₃ C₂H₅ 749 CH₂OCH₂CH₃ CH₃ CH₃ C₂H₅ 750 CH₂NH₂ CH₃ CH₃ C₂H₅ 751 (CH₂)₂COCH₃ CH₃ CH₃ C₂H₅ 752 phenyl CH₃ CH₃ C₂H₅ 753 2-F-phenyl CH₃ CH₃ C₂H₅ 754 3-F-phenyl CH₃ CH₃ C₂H₅ 755 4-F-phenyl CH₃ CH₃ C₂H₅ 756 2-Cl-phenyl CH₃ CH₃ C₂H₅ 757 3-Cl-phenyl CH₃ CH₃ C₂H₅ 758 4-Cl-phenyl CH₃ CH₃ C₂H₅ 759 2-OH-phenyl CH₃ CH₃ C₂H₅ 760 3-OH-phenyl CH₃ CH₃ C₂H₅ 761 4-OH-phenyl CH₃ CH₃ C₂H₅ 762 2-OCH₃-phenyl CH₃ CH₃ C₂H₅ 763 3-OCH₃-phenyl CH₃ CH₃ C₂H₅ 764 4-OCH₃-phenyl CH₃ CH₃ C₂H₅ 765 2-OCF₃-phenyl CH₃ CH₃ C₂H₅ 766 3-OCF₃-phenyl CH₃ CH₃ C₂H₅ 767 4-OCF₃-phenyl CH₃ CH₃ C₂H₅ 768 2-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 769 3-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 770 4-OCHF₂-phenyl CH₃ CH₃ C₂H₅ 771 2-CF₃-phenyl CH₃ CH₃ C₂H₅ 772 3-CF₃-phenyl CH₃ CH₃ C₂H₅ 773 4-CF₃-phenyl CH₃ CH₃ C₂H₅ 774 2-CH₃-phenyl CH₃ CH₃ C₂H₅ 775 3-CH₃-phenyl CH₃ CH₃ C₂H₅ 776 4-CH₃-phenyl CH₃ CH₃ C₂H₅ 777 2-NO₂-phenyl CH₃ CH₃ C₂H₅ 778 3-NO₂-phenyl CH₃ CH₃ C₂H₅ 779 4-NO₂-phenyl CH₃ CH₃ C₂H₅ 780 2-pyridyl CH₃ CH₃ C₂H₅ 781 3-pyridyl CH₃ CH₃ C₂H₅ 782 4-pyridyl CH₃ CH₃ C₂H₅ 783 cyclohexylamino CH₃ CH₃ C₂H₅ 784 cyclopentylamino CH₃ CH₃ C₂H₅ 785 H OCH₃ CH₃ C₂H₅ 786 CH₃ OCH₃ CH₃ C₂H₅ 787 C₂H₅ OCH₃ CH₃ C₂H₅ 788 n-C₃H₇ OCH₃ CH₃ C₂H₅ 789 i-C₃H₇ OCH₃ CH₃ C₂H₅ 790 n-C₄C₉ OCH₃ CH₃ C₂H₅ 791 s-C₄C₉ OCH₃ CH₃ C₂H₅ 792 i-C₄C₉ OCH₃ CH₃ C₂H₅ 793 t-C₄C₉ OCH₃ CH₃ C₂H₅ 794 CH₂Cl OCH₃ CH₃ C₂H₅ 795 CHCl₂ OCH₃ CH₃ C₂H₅ 796 CCl₃ OCH₃ CH₃ C₂H₅ 797 CH₂F OCH₃ CH₃ C₂H₅ 798 CHF₂ OCH₃ CH₃ C₂H₅ 799 CF₃ OCH₃ CH₃ C₂H₅ 800 CH₂CF₃ OCH₃ CH₃ C₂H₅ 801 CH₂OCH₃ OCH₃ CH₃ C₂H₅ 802 CH₂OCH₂CH₃ OCH₃ CH₃ C₂H₅ 803 CH₂NH₂ OCH₃ CH₃ C₂H₅ 804 (CH₂)₂COCH₃ OCH₃ CH₃ C₂H₅ 805 phenyl OCH₃ CH₃ C₂H₅ 806 2-F-phenyl OCH₃ CH₃ C₂H₅ 807 3-F-phenyl OCH₃ CH₃ C₂H₅ 808 4-F-phenyl OCH₃ CH₃ C₂H₅ 809 2-Cl-phenyl OCH₃ CH₃ C₂H₅ 810 3-Cl-phenyl OCH₃ CH₃ C₂H₅ 811 4-Cl-phenyl OCH₃ CH₃ C₂H₅ 812 2-OH-phenyl OCH₃ CH₃ C₂H₅ 813 3-OH-phenyl OCH₃ CH₃ C₂H₅ 814 4-OH-phenyl OCH₃ CH₃ C₂H₅ 815 2-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 816 3-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 817 4-OCH₃-phenyl OCH₃ CH₃ C₂H₅ 818 2-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 819 3-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 820 4-OCF₃-phenyl OCH₃ CH₃ C₂H₅ 821 2-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 822 3-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 823 4-OCHF₂-phenyl OCH₃ CH₃ C₂H₅ 824 2-CF₃-phenyl OCH₃ CH₃ C₂H₅ 825 3-CF₃-phenyl OCH₃ CH₃ C₂H₅ 826 4-CF₃-phenyl OCH₃ CH₃ C₂H₅ 827 2-CH₃-phenyl OCH₃ CH₃ C₂H₅ 828 3-CH₃-phenyl OCH₃ CH₃ C₂H₅ 829 4-CH₃-phenyl OCH₃ CH₃ C₂H₅ 830 2-NO₂-phenyl OCH₃ CH₃ C₂H₅ 831 3-NO₂-phenyl OCH₃ CH₃ C₂H₅ 832 4-NO₂-phenyl OCH₃ CH₃ C₂H₅ 833 2-pyridyl OCH₃ CH₃ C₂H₅ 834 3-pyridyl OCH₃ CH₃ C₂H₅ 835 4-pyridyl OCH₃ CH₃ C₂H₅ 836 cyclohexylamino OCH₃ CH₃ C₂H₅ 837 cyclopentylamino OCH₃ CH₃ C₂H₅ 838 H Cl CH₃ C₂H₅ 839 CH₃ Cl CH₃ C₂H₅ 840 C₂H₅ Cl CH₃ C₂H₅ 841 n-C₃H₇ Cl CH₃ C₂H₅ 842 i-C₃H₇ Cl CH₃ C₂H₅ 843 n-C₄C₉ Cl CH₃ C₂H₅ 844 s-C₄C₉ Cl CH₃ C₂H₅ 845 i-C₄C₉ Cl CH₃ C₂H₅ 846 t-C₄C₉ Cl CH₃ C₂H₅ 847 CH₂Cl Cl CH₃ C₂H₅ 848 CHCl₂ Cl CH₃ C₂H₅ 849 CCl₃ Cl CH₃ C₂H₅ 850 CH₂F Cl CH₃ C₂H₅ 851 CHF₂ Cl CH₃ C₂H₅ 852 CF₃ Cl CH₃ C₂H₅ 853 CH₂CF₃ Cl CH₃ C₂H₅ 854 CH₂OCH₃ Cl CH₃ C₂H₅ 855 CH₂OCH₂CH₃ Cl CH₃ C₂H₅ 856 CH₂NH₂ Cl CH₃ C₂H₅ 857 (CH₂)₂COCH₃ Cl CH₃ C₂H₅ 858 phenyl Cl CH₃ C₂H₅ 859 2-F-phenyl Cl CH₃ C₂H₅ 860 3-F-phenyl Cl CH₃ C₂H₅ 861 4-F-phenyl Cl CH₃ C₂H₅ 862 2-Cl-phenyl Cl CH₃ C₂H₅ 863 3-Cl-phenyl Cl CH₃ C₂H₅ 864 4-Cl-phenyl Cl CH₃ C₂H₅ 865 2-OH-phenyl Cl CH₃ C₂H₅ 866 3-OH-phenyl Cl CH₃ C₂H₅ 867 4-OH-phenyl Cl CH₃ C₂H₅ 868 2-OCH₃-phenyl Cl CH₃ C₂H₅ 869 3-OCH₃-phenyl Cl CH₃ C₂H₅ 870 4-OCH₃-phenyl Cl CH₃ C₂H₅ 871 2-OCF₃-phenyl Cl CH₃ C₂H₅ 872 3-OCF₃-phenyl Cl CH₃ C₂H₅ 873 4-OCF₃-phenyl Cl CH₃ C₂H₅ 874 2-OCHF₂-phenyl Cl CH₃ C₂H₅ 875 3-OCHF₂-phenyl Cl CH₃ C₂H₅ 876 4-OCHF₂-phenyl Cl CH₃ C₂H₅ 877 2-CF₃-phenyl Cl CH₃ C₂H₅ 878 3-CF₃-phenyl Cl CH₃ C₂H₅ 879 4-CF₃-phenyl Cl CH₃ C₂H₅ 880 2-CH₃-phenyl Cl CH₃ C₂H₅ 881 3-CH₃-phenyl Cl CH₃ C₂H₅ 882 4-CH₃-phenyl Cl CH₃ C₂H₅ 883 2-NO₂-phenyl Cl CH₃ C₂H₅ 884 3-NO₂-phenyl Cl CH₃ C₂H₅ 885 4-NO₂-phenyl Cl CH₃ C₂H₅ 886 2-pyridyl Cl CH₃ C₂H₅ 887 3-pyridyl Cl CH₃ C₂H₅ 888 4-pyridyl Cl CH₃ C₂H₅ 889 cyclohexylamino Cl CH₃ C₂H₅ 890 cyclopentylamino Cl CH₃ C₂H₅ 891 CH₃ CH₃ H C₂H₅ 892 C₂H₅ CH₃ H C₂H₅ 893 n-C₃H₇ CH₃ H C₂H₅ 894 i-C₃H₇ CH₃ H C₂H₅ 895 n-C₄C₉ CH₃ H C₂H₅ 896 s-C₄C₉ CH₃ H C₂H₅ 897 i-C₄C₉ CH₃ H C₂H₅ 898 t-C₄C₉ CH₃ H C₂H₅ 899 CH₂Cl CH₃ H C₂H₅ 900 CHCl₂ CH₃ H C₂H₅ 901 CCl₃ CH₃ H C₂H₅ 902 CH₂F CH₃ H C₂H₅ 903 CHF₂ CH₃ H C₂H₅ 904 CF₃ CH₃ H C₂H₅ 905 CH₂CF₃ CH₃ H C₂H₅ 906 CH₂OCH₃ CH₃ H C₂H₅ 907 CH₂OCH₂CH₃ CH₃ H C₂H₅ 908 CH₂NH₂ CH₃ H C₂H₅ 909 (CH₂)₂COCH₃ CH₃ H C₂H₅ 910 phenyl CH₃ H C₂H₅ 911 2-F-phenyl CH₃ H C₂H₅ 912 3-F-phenyl CH₃ H C₂H₅ 913 4-F-phenyl CH₃ H C₂H₅ 914 2-Cl-phenyl CH₃ H C₂H₅ 915 3-Cl-phenyl CH₃ H C₂H₅ 916 4-Cl-phenyl CH₃ H C₂H₅ 917 2-OH-phenyl CH₃ H C₂H₅ 918 3-OH-phenyl CH₃ H C₂H₅ 919 4-OH-phenyl CH₃ H C₂H₅ 920 2-OCH₃-phenyl CH₃ H C₂H₅ 921 3-OCH₃-phenyl CH₃ H C₂H₅ 922 4-OCH₃-phenyl CH₃ H C₂H₅ 923 2-OCF₃-phenyl CH₃ H C₂H₅ 924 3-OCF₃-phenyl CH₃ H C₂H₅ 925 4-OCF₃-phenyl CH₃ H C₂H₅ 926 2-OCHF₂-phenyl CH₃ H C₂H₅ 927 3-OCHF₂-phenyl CH₃ H C₂H₅ 928 4-OCHF₂-phenyl CH₃ H C₂H₅ 929 2-CF₃-phenyl CH₃ H C₂H₅ 930 3-CF₃-phenyl CH₃ H C₂H₅ 931 4-CF₃-phenyl CH₃ H C₂H₅ 932 2-CH₃-phenyl CH₃ H C₂H₅ 933 3-CH₃-phenyl CH₃ H C₂H₅ 934 4-CH₃-phenyl CH₃ H C₂H₅ 935 2-NO₂-phenyl CH₃ H C₂H₅ 936 3-NO₂-phenyl CH₃ H C₂H₅ 937 4-NO₂-phenyl CH₃ H C₂H₅ 938 2-pyridyl CH₃ H C₂H₅ 939 3-pyridyl CH₃ H C₂H₅ 940 4-pyridyl CH₃ H C₂H₅ 941 cyclohexylamino CH₃ H C₂H₅ 942 cyclopentylamino CH₃ H C₂H₅ 943 H OCH₃ H C₂H₅ 944 CH₃ OCH₃ H C₂H₅ 945 C₂H₅ OCH₃ H C₂H₅ 946 n-C₃H₇ OCH₃ H C₂H₅ 947 i-C₃H₇ OCH₃ H C₂H₅ 948 n-C₄C₉ OCH₃ H C₂H₅ 949 s-C₄C₉ OCH₃ H C₂H₅ 950 i-C₄C₉ OCH₃ H C₂H₅ 951 t-C₄C₉ OCH₃ H C₂H₅ 952 CH₂Cl OCH₃ H C₂H₅ 953 CHCl₂ OCH₃ H C₂H₅ 954 CCl₃ OCH₃ H C₂H₅ 955 CH₂F OCH₃ H C₂H₅ 956 CHF₂ OCH₃ H C₂H₅ 957 CF₃ OCH₃ H C₂H₅ 958 CH₂CF₃ OCH₃ H C₂H₅ 959 CH₂OCH₃ OCH₃ H C₂H₅ 960 CH₂OCH₂CH₃ OCH₃ H C₂H₅ 961 CH₂NH₂ OCH₃ H C₂H₅ 962 (CH₂)₂COCH₃ OCH₃ H C₂H₅ 963 phenyl OCH₃ H C₂H₅ 964 2-F-phenyl OCH₃ H C₂H₅ 965 3-F-phenyl OCH₃ H C₂H₅ 966 4-F-phenyl OCH₃ H C₂H₅ 967 2-Cl-phenyl OCH₃ H C₂H₅ 968 3-Cl-phenyl OCH₃ H C₂H₅ 969 4-Cl-phenyl OCH₃ H C₂H₅ 970 2-OH-phenyl OCH₃ H C₂H₅ 971 3-OH-phenyl OCH₃ H C₂H₅ 972 4-OH-phenyl OCH₃ H C₂H₅ 973 2-OCH₃-phenyl OCH₃ H C₂H₅ 974 3-OCH₃-phenyl OCH₃ H C₂H₅ 975 4-OCH₃-phenyl OCH₃ H C₂H₅ 976 2-OCF₃-phenyl OCH₃ H C₂H₅ 977 3-OCF₃-phenyl OCH₃ H C₂H₅ 978 4-OCF₃-phenyl OCH₃ H C₂H₅ 979 2-OCHF₂-phenyl OCH₃ H C₂H₅ 980 3-OCHF₂-phenyl OCH₃ H C₂H₅ 981 4-OCHF₂-phenyl OCH₃ H C₂H₅ 982 2-CF₃-phenyl OCH₃ H C₂H₅ 983 3-CF₃-phenyl OCH₃ H C₂H₅ 984 4-CF₃-phenyl OCH₃ H C₂H₅ 985 2-CH₃-phenyl OCH₃ H C₂H₅ 986 3-CH₃-phenyl OCH₃ H C₂H₅ 987 4-CH₃-phenyl OCH₃ H C₂H₅ 988 2-NO₂-phenyl OCH₃ H C₂H₅ 989 3-NO₂-phenyl OCH₃ H C₂H₅ 990 4-NO₂-phenyl OCH₃ H C₂H₅ 991 2-pyridyl OCH₃ H C₂H₅ 992 3-pyridyl OCH₃ H C₂H₅ 993 4-pyridyl OCH₃ H C₂H₅ 994 cyclohexylamino OCH₃ H C₂H₅ 995 cyclopentylamino OCH₃ H C₂H₅ 996 H Cl H C₂H₅ 997 CH₃ Cl H C₂H₅ 998 C₂H₅ Cl H C₂H₅ 999 n-C₃H₇ Cl H C₂H₅ 999 i-C₃H₇ Cl H C₂H₅ 1000 n-C₄C₉ Cl H C₂H₅ 1001 s-C₄C₉ Cl H C₂H₅ 1002 i-C₄C₉ Cl H C₂H₅ 1003 t-C₄C₉ Cl H C₂H₅ 1004 CH₂Cl Cl H C₂H₅ 1005 CHCl₂ Cl H C₂H₅ 1006 CCl₃ Cl H C₂H₅ 1007 CH₂F Cl H C₂H₅ 1008 CHF₂ Cl H C₂H₅ 1009 CF₃ Cl H C₂H₅ 1010 CH₂CF₃ Cl H C₂H₅ 1011 CH₂OCH₃ Cl H C₂H₅ 1012 CH₂OCH₂CH₃ Cl H C₂H₅ 1013 CH₂NH₂ Cl H C₂H₅ 1014 (CH₂)₂COCH₃ Cl H C₂H₅ 1015 phenyl Cl H C₂H₅ 1016 2-F-phenyl Cl H C₂H₅ 1017 3-F-phenyl Cl H C₂H₅ 1018 4-F-phenyl Cl H C₂H₅ 1019 2-Cl-phenyl Cl H C₂H₅ 1020 3-Cl-phenyl Cl H C₂H₅ 1021 4-Cl-phenyl Cl H C₂H₅ 1022 2-OH-phenyl Cl H C₂H₅ 1023 3-OH-phenyl Cl H C₂H₅ 1024 4-OH-phenyl Cl H C₂H₅ 1025 2-OCH₃-phenyl Cl H C₂H₅ 1026 3-OCH₃-phenyl Cl H C₂H₅ 1027 4-OCH₃-phenyl Cl H C₂H₅ 1028 2-OCF₃-phenyl Cl H C₂H₅ 1029 3-OCF₃-phenyl Cl H C₂H₅ 1030 4-OCF₃-phenyl Cl H C₂H₅ 1031 2-OCHF₂-phenyl Cl H C₂H₅ 1032 3-OCHF₂-phenyl Cl H C₂H₅ 1033 4-OCHF₂-phenyl Cl H C₂H₅ 1034 2-CF₃-phenyl Cl H C₂H₅ 1035 3-CF₃-phenyl Cl H C₂H₅ 1036 4-CF₃-phenyl Cl H C₂H₅ 1037 2-CH₃-phenyl Cl H C₂H₅ 1038 3-CH₃-phenyl Cl H C₂H₅ 1039 4-CH₃-phenyl Cl H C₂H₅ 1040 2-NO₂-phenyl Cl H C₂H₅ 1041 3-NO₂-phenyl Cl H C₂H₅ 1042 4-NO₂-phenyl Cl H C₂H₅ 1043 2-pyridyl Cl H C₂H₅ 1044 3-pyridyl Cl H C₂H₅ 1045 4-pyridyl Cl H C₂H₅ 1046 cyclohexylamino Cl H C₂H₅ 1047 cyclopentylamino Cl H C₂H₅ 1048 CH₃ CH₃ CH₃ i-C₃H₇ 1049 C₂H₅ CH₃ CH₃ i-C₃H₇ 1050 n-C₃H₇ CH₃ CH₃ i-C₃H₇ 1051 i-C₃H₇ CH₃ CH₃ i-C₃H₇ 1052 n-C₄H₉ CH₃ CH₃ i-C₃H₇ 1053 s-C₄H₉ CH₃ CH₃ i-C₃H₇ 1054 i-C₄H₉ CH₃ CH₃ i-C₃H₇ 1055 t-C₄H₉ CH₃ CH₃ i-C₃H₇ 1056 CH₂Cl CH₃ CH₃ i-C₃H₇ 1057 CHCl₂ CH₃ CH₃ i-C₃H₇ 1058 CCl₃ CH₃ CH₃ i-C₃H₇ 1059 CH₂F CH₃ CH₃ i-C₃H₇ 1060 CHF₂ CH₃ CH₃ i-C₃H₇ 1061 CF₃ CH₃ CH₃ i-C₃H₇ 1062 CH₂CF₃ CH₃ CH₃ i-C₃H₇ 1063 CH₂OCH₃ CH₃ CH₃ i-C₃H₇ 1064 CH₂OCH₂CH₃ CH₃ CH₃ i-C₃H₇ 1065 CH₂NH₂ CH₃ CH₃ i-C₃H₇ 1066 (CH₂)₂COCH₃ CH₃ CH₃ i-C₃H₇ 1067 phenyl CH₃ CH₃ i-C₃H₇ 1068 2-F-phenyl CH₃ CH₃ i-C₃H₇ 1069 3-F-phenyl CH₃ CH₃ i-C₃H₇ 1070 4-F-phenyl CH₃ CH₃ i-C₃H₇ 1071 2-Cl-phenyl CH₃ CH₃ i-C₃H₇ 1072 3-Cl-phenyl CH₃ CH₃ i-C₃H₇ 1073 4-Cl-phenyl CH₃ CH₃ i-C₃H₇ 1074 2-OH-phenyl CH₃ CH₃ i-C₃H₇ 1075 3-OH-phenyl CH₃ CH₃ i-C₃H₇ 1076 4-OH-phenyl CH₃ CH₃ i-C₃H₇ 1077 2-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1078 3-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1079 4-OCH₃-phenyl CH₃ CH₃ i-C₃H₇ 1080 2-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1081 3-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1082 4-OCF₃-phenyl CH₃ CH₃ i-C₃H₇ 1083 2-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1084 3-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1085 4-OCHF₂-phenyl CH₃ CH₃ i-C₃H₇ 1086 2-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1087 3-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1088 4-CF₃-phenyl CH₃ CH₃ i-C₃H₇ 1089 2-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1090 3-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1091 4-CH₃-phenyl CH₃ CH₃ i-C₃H₇ 1092 2-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1093 3-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1094 4-NO₂-phenyl CH₃ CH₃ i-C₃H₇ 1095 2-pyridyl CH₃ CH₃ i-C₃H₇ 1096 3-pyridyl CH₃ CH₃ i-C₃H₇ 1097 4-pyridyl CH₃ CH₃ i-C₃H₇ 1098 cyclohexylamino CH₃ CH₃ i-C₃H₇ 1099 cyclopentylamino CH₃ CH₃ i-C₃H₇ 1100 H OCH₃ CH₃ i-C₃H₇ 1101 CH₃ OCH₃ CH₃ i-C₃H₇ 1102 C₂H₅ OCH₃ CH₃ i-C₃H₇ 1103 n-C₃H₇ OCH₃ CH₃ i-C₃H₇ 1104 i-C₃H₇ OCH₃ CH₃ i-C₃H₇ 1105 n-C₄C₉ OCH₃ CH₃ i-C₃H₇ 1106 s-C₄C₉ OCH₃ CH₃ i-C₃H₇ 1107 i-C₄C₉ OCH₃ CH₃ i-C₃H₇ 1108 t-C₄C₉ OCH₃ CH₃ i-C₃H₇ 1109 CH₂Cl OCH₃ CH₃ i-C₃H₇ 1110 CHCl₂ OCH₃ CH₃ i-C₃H₇ 1111 CCl₃ OCH₃ CH₃ i-C₃H₇ 1112 CH₂F OCH₃ CH₃ i-C₃H₇ 1113 CHF₂ OCH₃ CH₃ i-C₃H₇ 1114 CF₃ OCH₃ CH₃ i-C₃H₇ 1115 CH₂CF₃ OCH₃ CH₃ i-C₃H₇ 1116 CH₂OCH₃ OCH₃ CH₃ i-C₃H₇ 1117 CH₂OCH₂CH₃ OCH₃ CH₃ i-C₃H₇ 1118 CH₂NH₂ OCH₃ CH₃ i-C₃H₇ 1119 (CH₂)₂COCH₃ OCH₃ CH₃ i-C₃H₇ 1120 phenyl OCH₃ CH₃ i-C₃H₇ 1121 2-F-phenyl OCH₃ CH₃ i-C₃H₇ 1122 3-F-phenyl OCH₃ CH₃ i-C₃H₇ 1123 4-F-phenyl OCH₃ CH₃ i-C₃H₇ 1124 2-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1125 3-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1126 4-Cl-phenyl OCH₃ CH₃ i-C₃H₇ 1127 2-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1128 3-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1129 4-OH-phenyl OCH₃ CH₃ i-C₃H₇ 1130 2-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1131 3-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1132 4-OCH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1133 2-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1134 3-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1135 4-OCF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1136 2-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇ 1137 3-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇ 1138 4-OCHF₂-phenyl OCH₃ CH₃ i-C₃H₇ 1139 2-CF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1140 3-CF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1141 4-CF₃-phenyl OCH₃ CH₃ i-C₃H₇ 1142 2-CH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1143 3-CH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1144 4-CH₃-phenyl OCH₃ CH₃ i-C₃H₇ 1145 2-NO₂-phenyl OCH₃ CH₃ i-C₃H₇ 1146 3-NO₂-phenyl OCH₃ CH₃ i-C₃H₇ 1147 4-NO₂-phenyl OCH₃ CH₃ i-C₃H₇ 1148 2-pyridyl OCH₃ CH₃ i-C₃H₇ 1149 3-pyridyl OCH₃ CH₃ i-C₃H₇ 1150 4-pyridyl OCH₃ CH₃ i-C₃H₇ 1151 cyclohexylamino OCH₃ CH₃ i-C₃H₇ 1152 cyclopentylamino OCH₃ CH₃ i-C₃H₇ 1153 H Cl CH₃ i-C₃H₇ 1154 CH₃ Cl CH₃ i-C₃H₇ 1155 C₂H₅ Cl CH₃ i-C₃H₇ 1156 n-C₃H₇ Cl CH₃ i-C₃H₇ 1157 i-C₃H₇ Cl CH₃ i-C₃H₇ 1158 n-C₄C₉ Cl CH₃ i-C₃H₇ 1159 s-C₄C₉ Cl CH₃ i-C₃H₇ 1160 i-C₄C₉ Cl CH₃ i-C₃H₇ 1161 t-C₄C₉ Cl CH₃ i-C₃H₇ 1162 CH₂Cl Cl CH₃ i-C₃H₇ 1163 CHCl₂ Cl CH₃ i-C₃H₇ 1164 CCl₃ Cl CH₃ i-C₃H₇ 1165 CH₂F Cl CH₃ i-C₃H₇ 1166 CHF₂ Cl CH₃ i-C₃H₇ 1167 CF₃ Cl CH₃ i-C₃H₇ 1168 CH₂CF₃ Cl CH₃ i-C₃H₇ 1169 CH₂OCH₃ Cl CH₃ i-C₃H₇ 1170 CH₂OCH₂CH₃ Cl CH₃ i-C₃H₇ 1171 CH₂NH₂ Cl CH₃ i-C₃H₇ 1172 (CH₂)₂COCH₃ Cl CH₃ i-C₃H₇ 1173 phenyl Cl CH₃ i-C₃H₇ 1174 2-F-phenyl Cl CH₃ i-C₃H₇ 1175 3-F-phenyl Cl CH₃ i-C₃H₇ 1176 4-F-phenyl Cl CH₃ i-C₃H₇ 1177 2-Cl-phenyl Cl CH₃ i-C₃H₇ 1178 3-Cl-phenyl Cl CH₃ i-C₃H₇ 1179 4-Cl-phenyl Cl CH₃ i-C₃H₇ 1180 2-OH-phenyl Cl CH₃ i-C₃H₇ 1181 3-OH-phenyl Cl CH₃ i-C₃H₇ 1182 4-OH-phenyl Cl CH₃ i-C₃H₇ 1183 2-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1184 3-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1185 4-OCH₃-phenyl Cl CH₃ i-C₃H₇ 1186 2-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1187 3-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1188 4-OCF₃-phenyl Cl CH₃ i-C₃H₇ 1189 2-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1190 3-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1191 4-OCHF₂-phenyl Cl CH₃ i-C₃H₇ 1192 2-CF₃-phenyl Cl CH₃ i-C₃H₇ 1193 3-CF₃-phenyl Cl CH₃ i-C₃H₇ 1194 4-CF₃-phenyl Cl CH₃ i-C₃H₇ 1195 2-CH₃-phenyl Cl CH₃ i-C₃H₇ 1196 3-CH₃-phenyl Cl CH₃ i-C₃H₇ 1197 4-CH₃-phenyl Cl CH₃ i-C₃H₇ 1198 2-NO₂-phenyl Cl CH₃ i-C₃H₇ 1199 3-NO₂-phenyl Cl CH₃ i-C₃H₇ 1200 4-NO₂-phenyl Cl CH₃ i-C₃H₇ 1201 2-pyridyl Cl CH₃ i-C₃H₇ 1202 3-pyridyl Cl CH₃ i-C₃H₇ 1203 4-pyridyl Cl CH₃ i-C₃H₇ 1204 cyclohexylamino Cl CH₃ i-C₃H₇ 1205 cyclopentylamino Cl CH₃ i-C₃H₇ 1206 CH₃ CH₃ H i-C₃H₇ 1207 C₂H₅ CH₃ H i-C₃H₇ 1208 n-C₃H₇ CH₃ H i-C₃H₇ 1209 i-C₃H₇ CH₃ H i-C₃H₇ 1210 n-C₄C₉ CH₃ H i-C₃H₇ 1211 s-C₄C₉ CH₃ H i-C₃H₇ 1212 i-C₄C₉ CH₃ H i-C₃H₇ 1213 t-C₄C₉ CH₃ H i-C₃H₇ 1214 CH₂Cl CH₃ H i-C₃H₇ 1215 CHCl₂ CH₃ H i-C₃H₇ 1116 CCl₃ CH₃ H i-C₃H₇ 1217 CH₂F CH₃ H i-C₃H₇ 1218 CHF₂ CH₃ H i-C₃H₇ 1219 CF₃ CH₃ H i-C₃H₇ 1220 CH₂CF₃ CH₃ H i-C₃H₇ 1221 CH₂OCH₃ CH₃ H i-C₃H₇ 1222 CH₂OCH₂CH₃ CH₃ H i-C₃H₇ 1223 CH₂NH₂ CH₃ H i-C₃H₇ 1224 (CH₂)₂COCH₃ CH₃ H i-C₃H₇ 1225 phenyl CH₃ H i-C₃H₇ 1226 2-F-phenyl CH₃ H i-C₃H₇ 1227 3-F-phenyl CH₃ H i-C₃H₇ 1228 4-F-phenyl CH₃ H i-C₃H₇ 1229 2-Cl-phenyl CH₃ H i-C₃H₇ 1230 3-Cl-phenyl CH₃ H i-C₃H₇ 1231 4-Cl-phenyl CH₃ H i-C₃H₇ 1232 2-OH-phenyl CH₃ H i-C₃H₇ 1233 3-OH-phenyl CH₃ H i-C₃H₇ 1234 4-OH-phenyl CH₃ H i-C₃H₇ 1235 2-OCH₃-phenyl CH₃ H i-C₃H₇ 1236 3-OCH₃-phenyl CH₃ H i-C₃H₇ 1237 4-OCH₃-phenyl CH₃ H i-C₃H₇ 1238 2-OCF₃-phenyl CH₃ H i-C₃H₇ 1239 3-OCF₃-phenyl CH₃ H i-C₃H₇ 1240 4-OCF₃-phenyl CH₃ H i-C₃H₇ 1241 2-OCHF₂-phenyl CH₃ H i-C₃H₇ 1242 3-OCHF₂-phenyl CH₃ H i-C₃H₇ 1243 4-OCHF₂-phenyl CH₃ H i-C₃H₇ 1244 2-CF₃-phenyl CH₃ H i-C₃H₇ 1245 3-CF₃-phenyl CH₃ H i-C₃H₇ 1246 4-CF₃-phenyl CH₃ H i-C₃H₇ 1247 2-CH₃-phenyl CH₃ H i-C₃H₇ 1248 3-CH₃-phenyl CH₃ H i-C₃H₇ 1249 4-CH₃-phenyl CH₃ H i-C₃H₇ 1250 2-NO₂-phenyl CH₃ H i-C₃H₇ 1251 3-NO₂-phenyl CH₃ H i-C₃H₇ 1252 4-NO₂-phenyl CH₃ H i-C₃H₇ 1253 2-pyridyl CH₃ H i-C₃H₇ 1254 3-pyridyl CH₃ H i-C₃H₇ 1255 4-pyridyl CH₃ H i-C₃H₇ 1256 cyclohexylamino CH₃ H i-C₃H₇ 1257 cyclopentylamino CH₃ H i-C₃H₇ 1258 H OCH₃ H i-C₃H₇ 1259 CH₃ OCH₃ H i-C₃H₇ 1260 C₂H₅ OCH₃ H i-C₃H₇ 1261 n-C₃H₇ OCH₃ H i-C₃H₇ 1262 i-C₃H₇ OCH₃ H i-C₃H₇ 1263 n-C₄C₉ OCH₃ H i-C₃H₇ 1264 s-C₄C₉ OCH₃ H i-C₃H₇ 1265 i-C₄C₉ OCH₃ H i-C₃H₇ 1266 t-C₄C₉ OCH₃ H i-C₃H₇ 1267 CH₂Cl OCH₃ H i-C₃H₇ 1268 CHCl₂ OCH₃ H i-C₃H₇ 1269 CCl₃ OCH₃ H i-C₃H₇ 1270 CH₂F OCH₃ H i-C₃H₇ 1271 CHF₂ OCH₃ H i-C₃H₇ 1272 CF₃ OCH₃ H i-C₃H₇ 1273 CH₂CF₃ OCH₃ H i-C₃H₇ 1274 CH₂OCH₃ OCH₃ H i-C₃H₇ 1275 CH₂OCH₂CH₃ OCH₃ H i-C₃H₇ 1276 CH₂NH₂ OCH₃ H i-C₃H₇ 1277 (CH₂)₂COCH₃ OCH₃ H i-C₃H₇ 1278 phenyl OCH₃ H i-C₃H₇ 1279 2-F-phenyl OCH₃ H i-C₃H₇ 1280 3-F-phenyl OCH₃ H i-C₃H₇ 1281 4-F-phenyl OCH₃ H i-C₃H₇ 1282 2-Cl-phenyl OCH₃ H i-C₃H₇ 1283 3-Cl-phenyl OCH₃ H i-C₃H₇ 1284 4-Cl-phenyl OCH₃ H i-C₃H₇ 1285 2-OH-phenyl OCH₃ H i-C₃H₇ 1286 3-OH-phenyl OCH₃ H i-C₃H₇ 1287 4-OH-phenyl OCH₃ H i-C₃H₇ 1288 2-OCH₃-phenyl OCH₃ H i-C₃H₇ 1289 3-OCH₃-phenyl OCH₃ H i-C₃H₇ 1290 4-OCH₃-phenyl OCH₃ H i-C₃H₇ 1291 2-OCF₃-phenyl OCH₃ H i-C₃H₇ 1292 3-OCF₃-phenyl OCH₃ H i-C₃H₇ 1293 4-OCF₃-phenyl OCH₃ H i-C₃H₇ 1294 2-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1295 3-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1296 4-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1297 2-CF₃-phenyl OCH₃ H i-C₃H₇ 1298 3-CF₃-phenyl 0CH₃ H i-C₃H₇ 1299 4-CF₃-phenyl OCH₃ H i-C₃H₇ 1300 2-CH₃-phenyl OCH₃ H i-C₃H₇ 1301 3-CH₃-phenyl OCH₃ H i-C₃H₇ 1302 4-CH₃-phenyl OCH₃ H i-C₃H₇ 1303 2-NO₂-phenyl OCH₃ H i-C₃H₇ 1304 3-NO₂-phenyl OCH₃ H i-C₃H₇ 1305 4-NO₂-phenyl OCH₃ H i-C₃H₇ 1306 2-pyridyl OCH₃ H i-C₃H₇ 1307 3-pyridyl OCH₃ H i-C₃H₇ 1308 4-pyridyl OCH₃ H i-C₃H₇ 1309 cyclohexylamino OCH₃ H i-C₃H₇ 1310 cyclopentylamino OCH₃ H i-C₃H₇ 1311 H Cl H i-C₃H₇ 1312 CH₃ Cl H i-C₃H₇ 1313 C₂H₅ Cl H i-C₃H₇ 1314 n-C₃H₇ Cl H i-C₃H₇ 1315 i-C₃H₇ Cl H i-C₃H₇ 1316 n-C₄C₉ Cl H i-C₃H₇ 1317 s-C₄C₉ Cl H i-C₃H₇ 1318 i-C₄C₉ Cl H i-C₃H₇ 1319 t-C₄C₉ Cl H i-C₃H₇ 1320 CH₂Cl Cl H i-C₃H₇ 1321 CHCl₂ Cl H i-C₃H₇ 1322 CH₃ Cl H i-C₃H₇ 1323 CH₂F Cl H i-C₃H₇ 1324 CHF₂ Cl H i-C₃H₇ 1325 CF₃ Cl H i-C₃H₇ 1326 CH₂CF₃ Cl H i-C₃H₇ 1327 CH₂OCH₃ Cl H i-C₃H₇ 1328 CH₂OCH₂CH₃ Cl H i-C₃H₇ 1329 CH₂NH₂ Cl H i-C₃H₇ 1330 (CH₂)₂COCH₃ Cl H i-C₃H₇ 1331 phenyl Cl H i-C₃H₇ 1332 2-F-phenyl Cl H i-C₃H₇ 1333 3-F-phenyl Cl H i-C₃H₇ 1334 4-F-phenyl Cl H i-C₃H₇ 1335 2-Cl-phenyl Cl H i-C₃H₇ 1336 3-Cl-phenyl Cl H i-C₃H₇ 1337 4-Cl-phenyl Cl H i-C₃H₇ 1338 2-OH-phenyl Cl H i-C₃H₇ 1339 3-OH-phenyl Cl H i-C₃H₇ 1340 4-OH-phenyl Cl H i-C₃H₇ 1341 2-OCH₃-phenyl Cl H i-C₃H₇ 1342 3-OCH₃-phenyl Cl H i-C₃H₇ 1343 4-OCH₃-phenyl Cl H i-C₃H₇ 1344 2-OCF₃-phenyl Cl H i-C₃H₇ 1345 3-OCF₃-phenyl OCH₃ H i-C₃H₇ 1346 4-OCF₃-phenyl OCH₃ H i-C₃H₇ 1347 2-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1348 3-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1349 4-OCHF₂-phenyl OCH₃ H i-C₃H₇ 1350 2-CF₃-phenyl OCH₃ H i-C₃H₇ 1351 3-CF₃-phenyl OCH₃ H i-C₃H₇ 1352 4-CF₃-phenyl OCH₃ H i-C₃H₇ 1353 2-CH₃-phenyl OCH₃ H i-C₃H₇ 1353 3-CH₃-phenyl OCH₃ H i-C₃H₇ 1354 4-CH₃-phenyl OCH₃ H i-C₃H₇ 1355 H CH₃ H H 1356 3-NO₂-phenyl OCH₃ H i-C₃H₇ 1357 H CH₃ CH₃ CH₃ 1358 2-pyridyl OCH₃ H i-C₃H₇ 1359 H CH₃ CH₃ C₂H₅ 1360 H CH₃ H C₂H₅ 1361 H CH₃ CH₃ i-C₃H₇ 1362 H CH₃ H i-C₃H₇ 1363 H CH₃ H CH₃

Examples of benzimidazol-5-ylcarbonyl derivatives of pyrazoles (compounds I-3=compounds I where X=C—R³ and Y=N—R⁴) which are particularly preferred according to the invention are the compounds listed in Tables 40 to 58.

TABLE 40 Compounds I-3a.1 to I-3a.1363

I-3a

Compounds of the formula I-3a, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 41 Compounds I-3b.1 to I-3b.1363

I-3b

Compounds of the formula I-3b, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 42 Compounds I-3c.1 to I-3c.1363

I-3c

Compounds of the formula I-3c, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 43 Compounds I-3d.1 to I-3d.1363

I-3d

Compounds of the formula I-3d, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 44 Compounds I-3e.1 to I-3e.1363

I-3e

Compounds of the formula I-3e, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 45 Compounds I-3f.1 to I-3f.1363

I-3f

Compounds of the formula I-3f, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 46 Compounds I-3g.1 to I-3g.1363

I-3g

Compounds of the formula I-3g, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 47 Compounds I-3h.1 to I-3h.1363

I-3h

Compounds of the formula I-3h, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 48 Compounds I-3i.1 to I-3i.1363

I-3i

Compounds of the formula I-3i, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 49 Compounds I-3k.1 to I-3k.1363

I-3k

Compounds of the formula I-3k, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 50 Compounds I-3l.1 to I-3l.1363

I-3l

Compounds of the formula I-3l, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 51 Compounds I-3m.1 to I-3m.1363

I-3m

Compounds of the formula I-3m, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 52 Compounds I-3n.1 to I-3n.1363

I-3n

Compounds of the formula I-3n, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 53 Compounds I-3o.1 to I-3o.1363

I-3o

Compounds of the formula I-3o, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 54 Compounds I-3p.1 to I-3p.1363

I-3p

Compounds of the formula I-3p, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 55 Compounds I-3q.1 to I-3q.1363

I-3q

Compounds of the formula I-3q, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 56 Compounds I-3r.1 to I-3r.1363

I-3r

Compounds of the formula I-3r, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 57 Compounds I-3s.1 to I-3s.1363

I-3s

Compounds of the formula I-3s, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE 58 Compounds I-3t.1 to I-3t.1363

I-3t

Compounds of the formula I-3t, in which the substituents R¹, R², R³ and R⁴ for each individual compound correspond in each case to one row of Table B.

TABLE C R¹ R² X Y 1 H H N S 2 CH₃ H N S 3 Cl H N S 4 OCH₃ H N S 5 SCH₃ H N S 6 S(O)₂CH₃ H N S 7 H Cl N S 8 CH₃ Cl N S 9 Cl Cl N S 10 OCH₃ Cl N S 11 SCH₃ Cl N S 12 S(O)₂CH₃ Cl N S 13 H CH₃ N S 14 CH₃ CH₃ N S 15 Cl CH₃ N S 16 OCH₃ CH₃ N S 17 SCH₃ CH₃ N S 18 S(O)₂CH₃ CH₃ N S 19 H H N NH 20 CH₃ H N NH 21 Cl H N NH 22 OCH₃ H N NH 23 SCH₃ H N NH 24 S(O)₂CH₃ H N NH 25 H Cl N NH 26 CH₃ Cl N NH 27 Cl Cl N NH 28 OCH₃ Cl N NH 29 SCH₃ Cl N NH 30 S(O)₂CH₃ Cl N NH 31 H CH₃ N NH 32 CH₃ CH₃ N NH 33 Cl CH₃ N NH 34 OCH₃ CH₃ N NH 35 SCH₃ CH₃ N NH 36 S(O)₂CH₃ CH₃ N NH 37 H H N NCH₃ 38 CH₃ H N NCH₃ 39 Cl H N NCH₃ 40 OCH₃ H N NCH₃ 41 SCH₃ H N NCH₃ 42 S(O)₂CH₃ H N NCH₃ 43 H Cl N NCH₃ 44 CH₃ Cl N NCH₃ 45 Cl Cl N NCH₃ 46 OCH₃ Cl N NCH₃ 47 SCH₃ Cl N NCH₃ 48 S(O)₂CH₃ Cl N NCH₃ 49 H CH₃ N NCH₃ 50 CH₃ CH₃ N NCH₃ 51 Cl CH₃ N NCH₃ 52 OCH₃ CH₃ N NCH₃ 53 SCH₃ CH₃ N NCH₃ 54 S(O)₂CH₃ CH₃ N NCH₃ 55 H H N NC₂H₅ 56 CH₃ H N NC₂H₅ 57 Cl H N NC₂H₅ 58 OCH₃ H N NC₂H₅ 59 SCH₃ H N NC₂H₅ 60 S(O)₂CH₃ H N NC₂H₅ 61 H Cl N NC₂H₅ 62 CH₃ Cl N NC₂H₅ 63 Cl Cl N NC₂H₅ 64 OCH₃ Cl N NC₂H₅ 65 SCH₃ Cl N NC₂H₅ 66 S(O)₂CH₃ Cl N NC₂H₅ 67 H CH₃ N NC₂H₅ 68 CH₃ CH₃ N NC₂H₅ 69 Cl CH₃ N NC₂H₅ 70 OCH₃ CH₃ N NC₂H₅ 71 SCH₃ CH₃ N NC₂H₅ 72 S(O)₂CH₃ CH₃ N NC₂H₅ 73 H H N N-i-C₃H₇ 74 CH₃ H N N-i-C₃H₇ 75 Cl H N N-i-C₃H₇ 76 OCH₃ H N N-i-C₃H₇ 77 SCH₃ H N N-i-C₃H₇ 78 S(O)₂CH₃ H N N-i-C₃H₇ 79 H Cl N N-i-C₃H₇ 80 CH₃ Cl N N-i-C₃H₇ 81 Cl Cl N N-i-C₃H₇ 82 OCH₃ Cl N N-i-C₃H₇ 83 SCH₃ Cl N N-i-C₃H₇ 84 S(O)₂CH₃ Cl N N-i-C₃H₇ 85 H CH₃ N N-i-C₃H₇ 86 CH₃ CH₃ N N-i-C₃H₇ 87 Cl CH₃ N N-i-C₃H₇ 88 OCH₃ CH₃ N N-i-C₃H₇ 89 SCH₃ CH₃ N N-i-C₃H₇ 90 S(O)₂CH₃ CH₃ N N-i-C₃H₇

Other examples of benzothiadiazol-5-ylcarbonyl derivatives of pyrazoles (X=N, Y=S) and benzotriazol-5-ylcarbonyl derivatives of pyrazoles (X=N, Y=N—R⁴) which are preferred according to the invention are the compounds listed in Tables 59 to 77 (compounds I-4).

TABLE 59 Compounds I-4a.1 to I-4a.90

I-4a

Compounds of the formula I-4a, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 60 Compounds I-4b.1 to I-4b.90

I-4b

Compounds of the formula I-4b, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 61 Compounds I-4c.1 to I-4c.90

I-4c

Compounds of the formula I-4c, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 62 Compounds I-4d.1 to I-4d.90

I-4d

Compounds of the formula I-4d, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 63 Compounds I-4e.1 to I-4e.90

I-4e

Compounds of the formula I-4e, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 64 Compounds I-4f.1 to I-4f.90

I-4f

Compounds of the formula I-4f, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 65 Compounds I-4g.1 to I-4g.90

I-4g

Compounds of the formula I-4g, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 66 Compounds I-4h.1 to I-4h.90

I-4h

Compounds of the formula I-4h, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 67 Compounds I-4i.1 to I-4i.90

I-4i

Compounds of the formula I-4i, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 68 Compounds I-4k.1 to I-4k.90

I-4k

Compounds of the formula I-4k, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 69 Compounds I-4l.1 to I-4l.90

I-4l

Compounds of the formula I-4l, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 70 Compounds I-4m.1 to I-4m.90

I-4m

Compounds of the formula I-4m, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 71 Compounds I-4n.1 to I-4n.90

I-4n

Compounds of the formula I-4n, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 72 Compounds I-4o.1 to I-4o.90

I-4o

Compounds of the formula I-4o, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 73 Compounds I-4p.1 to I-4p.90

I-4p

Compounds of the formula I-4p, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 74 Compounds I-4q.1 to I-4q.90

I-4q

Compounds of the formula I-4q, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 75 Compounds I-4r.1 to I-4r.90

I-4r

Compounds of the formula I-4r, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 76 Compounds I-4s.1 to I-4s.90

I-4s

Compounds of the formula I-4s, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

TABLE 77 Compounds I-4t.1 to I-4t.90

I-4t

Compounds of the formula I-4t, in which the substituents R¹, R², X and Y for each individual compound correspond in each case to one row of Table C.

Compounds of the formula I where R⁸ is hydroxyl are prepared by reacting an activated carboxylic acid IVb or a carboxylic acid IVa, which is preferably activated in situ, with 5-hydroxypyrazole of the formula III to give the acylation product, followed by rearrangement.

L¹ is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.

The activated carboxylic acid IVa can be employed directly, such as in the case of the benzoyl halides, or be generated in situ, for example using a carbodiimide, such as ethyl-(3′-dimethylaminopropyl)carbodiimide, dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. Here, the reactants and the auxiliary base are advantageously employed in equimolar amounts. In some cases, it may be advantageous to employ a slight excess of the auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on IVa or IVb.

Suitable auxiliary bases are tertiary alkylamines, pyridine, 4-dimethylaminopyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

If the activated carboxylic acid component used is a halide, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reactant. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction has gone to completion. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude ester can be employed for the rearrangement without further purification.

The rearrangement of the esters to give the compounds of the formula I is advantageously carried out at 20-100° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount or an up to 4-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in twice the equimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetonecyanohydrin or trimethylsilyl cyanide. They are employed in an amount of 1-50 mol percent, based on the ester. Preference is given to using acetonecyanohydrin or trimethylsilyl cyanide, for example in an amount of 5-15, preferably about 10, mol percent, based on the ester.

Work-up can be carried out in a manner known per se. The reaction mixture is, for example, acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the precipitate that is formed is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

B. Preparation of compounds of the formula I where R⁸=halogen is carried out by reacting pyrazole derivatives of the formula I (where R⁸=hydroxyl) with halogenating agents:

Here and below, “compound Ia” is a compound of the formula I where Pz is a pyrazolyl radical of the formula IIa and, correspondingly, compound Ib is a compound of the formula I where Pz is a radical IIb.

Suitable halogenating agents are, for example phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.

C. Preparation of compounds of the formula I where R⁸=OR¹¹, OSO₂R¹², OPOR¹³R¹⁴ or OPSR¹³R¹⁴ by reacting pyrazole derivatives of the formula I (where R⁸=hydroxyl) with alkylating, sulfonylating or phosphonylating agents Vα, Vβ, Vγ and Vδ, respectively.

L² is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.

When preparing compounds of the formula I where R⁸=OR¹¹ from compounds of the formula I where R⁸=OH, the reaction is preferably carried out in the presence of a base.

Reactants and base are expediently employed in equimolar amounts. In certain cases, a slight excess of base, for example 1.1-1.5 molar equivalents, based on I, may be advantageous.

Suitable bases are tertiary amines, pyridines, alkali metal carbonates or alkali metal hydrides. Suitable solvents are, for example, chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons such as toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane or dimethoxyethane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate and mixtures thereof.

If, instead of the alcohol I (R⁸=OH), halides (R⁸=halogen) or activated alcohols such as mesylate or tosylate (R⁸=OSO₂CH₃ or OSO₂-tolyl) are employed for the derivatization, it may be expedient to cool the reaction mixture to from 0 to 10° C. when adding the reaction partner. Subsequently, the mixture is stirred at 20-100° C., preferably at 20-75° C., until the reaction has gone to completion.

Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents suitable for this purpose are, in particular, solvents such as methylene chloride, ethyl acetate, methyl tert-butyl ether or diethyl ether. After drying of the organic phase and removal of the solvent, the crude product can, if desired, be purified by silica gel column chromatography. Suitable mobile phases are solvents such as methylene chloride, ethyl acetate, cyclohexane, petroleum ether, methanol, acetone or chloroform and mixtures thereof.

Compounds of the formula Vα, Vβ, Vγ or Vδ can be employed directly, such as in the case of the carbonyl halides, or be generated in situ, for example activated carboxylic acids (using carboxylic acid and dicyclohexylcarbodiimide, etc.).

D. Compounds of the formula I where R⁸=OR¹¹, SR¹¹, POR¹³R¹⁴, NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl are prepared by reacting compounds of the formula I where R⁸=halogen, OSO₂R¹² with compounds of the formula VIα, VIβ, VIγ, VIδ, VIε or VIη, if appropriate in the presence of a base or with prior formation of salt.

E. Compounds of the formula I where R⁸=SOR¹², SO₂R¹² are prepared, for example, by reacting compounds of the formula I where R⁸=SR¹² with an oxidizing agent.

Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.

For the reactions mentioned under points B to E, the following conditions apply:

The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.

If appropriate, it may be advantageous to carry out the reactions in the presence of a base. Reactants and base are advantageously employed in equimolar amounts.

With respect to the processes C and D, it may, in certain cases, be advantageous to employ an excess of base, for example 1.5 to 3 molar equivalents, in each case based on the starting material.

Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to give the product.

Depending on the reaction conditions, in the processes B to D the compounds Ia, Ib, or mixtures of these can be formed. The latter can be separated by classic separation methods, for example crystallization, chromatography, etc.

F. The preparation of compounds of the formula I where Pz is a group of the formula IIa can also be carried out by reacting a metallated pyrazole derivative of the formula VII with a carboxylic acid derivative of the formula IVa:

Here, M is a metal, in particular an alkali metal, such as lithium or sodium, an alkaline earth metal, such as magnesium, or a transition metal, such as palladium, nickel, etc., and L¹ is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, such as mesylate, haloalkylsulfonate, such as triflate or cyanide. Preferably, R⁸ does not have any acidic hydrogen atoms.

The reaction is generally carried out at temperatures from −100° C. to the reflux temperature of the reaction mixture. Suitable solvents are. inert aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran. The compounds of the formula IVa are generally employed in excess; however, it may also be advantageous to employ them in equimolar amounts or in excess. Work-up is carried out to afford the product.

The metallated pyrazole derivatives of the formula VII can be formed in a manner known per se by reacting pyrazoles which are halogenated in the 4 position with metals such as lithium, sodium, magnesium, etc., or with organometallic compounds, for example butyllithium. However, it is also possible to metallate pyrazoles which are linked in the 4 position to hydrogen directly, for example using the abovementioned metals or organometallic compounds. The reactions are generally carried out in an inert aprotic solvent, preferably in ethers, such as diethyl ether, tetrahydrofuran, etc. The reaction temperature is in the range from −100° C. to the boiling point of the reaction mixture. The compounds of the formula VII are preferably generated in situ and reacted directly.

The 5-hydroxypyrazoles of the formula III used as starting materials are known or can be prepared by processes known per se as described, for example, in EP-A 240 001, in J. Chem. Soc. 315, (1997), p. 383, J. Prakt. Chem. 315, (1973), p. 382 (see also the reviews in Advances Heterocycle. Chem. 48, (1990), pp. 223-299 and Katritzky, Rees (Eds.), Comprehensive Heterocyclic Chem. Vol. 5, Pergamon Press 1984, Oxford, pp. 167-343 and literature cited therein). Furthermore, 1,3-dimethyl-5-hydroxypyrazole is a compound which is commercially available.

The alkylating agents Vα, sulfonylating agents Vβ, phosphonylating agents Vγ and Vδ, and the compounds VIα, VIβ, VIγ, VIδ and VIε are likewise known, or they can be prepared by known processes.

The carboxylic acids of the formula IVa and their activated derivatives IVb are either known from the literature, or they can be prepared analogously to known processes.

Scheme 1 shows a customary route to benzothiazol-5-carboxylic acids (compounds IV-1).

In the formula IV-1, R is hydrogen (compound IV-1a) or a hydrocarbon radical which can be hydrolyzed, for example methyl (compound IV-1b). Compounds of the formula IV-1 can be prepared, for example, according to reaction step a) by condensation of ortho-aminothiophenols of the formula VIII (R′=H) or of ortho-aminothioethers of the formula VIII (R′=C₁-C₄-alkyl, for example methyl), using a carboxylic acid equivalent “R³—CO₂H” i.e. a carboxylic acid R³CO₂H or activated derivatives R³COL¹, R³C(L³)₃ thereof where L¹ is a reactive leaving group and L³ is a C₁-C₄-alkoxy group. Examples of L¹ are chlorine, bromine, carboxylate, such as acetate, trifluoroacetate, N-heterocyclyl, such as imidazolyl, pyridyl etc. Examples of R³COL¹ and R³C(L³)₃ are acyl halides, carboxylic esters and carboxylic anhydrides, and the ortho esters of the carboxylic acids R³CO₂H.

The condensation reaction a) is preferably carried out under neutral to acidic reaction conditions, preferably in the presence of an inorganic or organic acid, for example hydrochloric acid, sulfuric acid, p-toluenesulfonic acid and pyridinium p-toluenesulfonate, in an organic solvent at 0-150° C., preferably in the range from 20 to 120° C. Suitable solvents are, in particular, saturated hydrocarbons, halogenated hydrocarbons, aromatic hydrocarbons, such as benzene, aliphatic ethers, such as diethyl ether and tert-butyl methyl ether, or pyridine. For the preparation of benzothiazoles from o-aminothiophenols or corresponding thiomethyl ethers, see also Houben-Weyl, Methoden der Organischen Chemie, Vol. E 8b, pp.869-871.

Step a) can also be carried out in two steps, by initially converting the amino function in VIII with a carboxylic acid R⁹—COOH or a derivative thereof into the carboxamide, which is subsequently cyclized to give the benzothiazole of the formula IV-1.

The conversion into the amide is carried out under the conditions which are customary for amide formation, for example by reacting an acid in the presence of a water-binding agent. Cyclization succeeds with Lewis acids or phosgene. In this case, the cyclization is preferably carried out in an inert organic solvent, for example an aliphatic or aromatic hydrocarbon, or in a halogenated hydrocarbon.

According to Scheme 1, ortho-aminothiophenols of the formula VIII (R′=H) can be prepared starting with 3-nitrotoluenes of the formula IX. Their methyl group can be oxidized in a known manner, catalytically or stoichiometrically, to give the carboxylic acid (step b). Suitable oxidizing agents are, for example, metal oxides of transition metals, for example manganese dioxide, chromium trioxide and their anionic complex salts, for example sodium dichromate or chromyl chloride, pyridinium chromate, furthermore oxidizing acids, for example HNO₃, oxidizing gases, such as oxygen or chlorine, if appropriate in the presence of transition metals (or salts thereof, for example oxides or chlorides) as catalysts. Depending on the solubility of the compound to be oxidized and depending on the oxidizing agent used, the reaction is preferably carried out in aqueous solutions, monophasic systems of water and water-miscible organic solvents or in multiphasic systems of water and organic solvents with phase-transfer catalysis. Depending on the chosen oxidizing agent, the oxidation is generally carried out in the range from −15 to +150° C., preferably in the range from 0 to 100° C. For the oxidation of aromatic methyl groups to benzoic acids, see, for example, Houben-Weyl: “Methoden der organischen Chemie”, Vol. V, IV/1a, 1981; Vol. VIII 1952; E. Bengtsson, Acta Chem. Scand. 7 (1953), 774; Singer et al., Org. Synth. Coll. Vol III, 1955, 740; B. A. S. Hay et al., Can. J. Chem. 43 (1965), 1306).

The resulting 3-nitrobenzoic acid derivatives are subsequently, in step c), reduced to the 3-aminobenzoic acids. The selective reduction of aromatic nitro groups in the presence of carboxylic acid groups is known in principle. Suitable reducing agents are, for example, hydrazines, metal hydrides, such as aluminum hydride, and complex compounds derived therefrom, such as lithium aluminium hydride, diisobutylaluminum hydride or boranes. The preferred reducing agent is hydrogen in the presence of catalytic amounts of transition metals, for example Ni, Pd, Pt, Ru or Rh, which may be employed in supported form, for example on active carbon, in the form of activated metals, for example Raney nickel, or in the form of soluble complex compounds. Suitable solvents for the reduction are, depending on the solubility of the substrate to be hydrogenated and the chosen reducing agent, C₁-C₄-alkohols, such as methanol, ethanol, n-propanol, isopropanol or n-butanol, halogenated C₁-C₆-hydrocarbons, such as dichloromethane, trichloromethane, trichloroethane, trichloroethylene, aromatic hydrocarbons, such as benzene, toluene, xylenes, chlorobenzene, aqueous solutions of inorganic or organic acids, such as aqueous hydrochloric acid. The reduction is usually carried out in the range from −15 to +100° C., preferably in the range from 0 to 40° C. The reduction with hydrogen is usually carried out at a hydrogen pressure in the range from 1 to 50 bar, preferably in the range from 1 to 10 bar. For the catalytic hydrogenation of aromatic nitro groups, see, for example, Rylander in “Catalytic Hydrogenation over Platinum Metals”, Academic press, New York, 1967, 168-202; Furst et al., Chem. Rev. 65 (1965), 52; Tepko et al., J. Org. Chem. 45 (1980), 4992.

The resulting m-aminobenzoic acids of the formula Xa (R=H) are then, in a further reaction step d), reacted with an organic isothiocyanate (in scheme 1 methyl isothiocyanate) to give a substituted thiourea derivative which, without further isolation, is cyclized oxidatively to give the benzothiazole-5-carboxylic acid of the formula IX-1a (in scheme 1 with R³=NH—CH₃).

The first reaction step in step d), i.e. the conversion of the m-aminobenzoic acid of the formula Xa into the substituted urea is carried out by reaction with a C₁-C₆-alkyl isothiocyanate or an unsubstituted or substituted phenyl isothiocyanate in an anhydrous organic solvent at from −15° C. to 150° C., preferably in the range from −15° C. to 100° C. Suitable solvents are, for example, aliphatic or cycloaliphatic hydrocarbons, such as n-hexane or cyclohexane, halogenated hydrocarbons, such as dichloromethane, trichloromethane, trichloroethane, trichloroethylene, aromatic hydrocarbons, such as benzene or anisole, dialkyl ethers or cyclic ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, anhydrous carboxylic acids, such as glacial acetic acid, or pyridine. For the preparation of substituted thioureas see, for example: F. Kurzer, Org. Synth. 31 (1951), 21; R. R. Gupta et al., Synth. Commun. 17(2) (1987), 229-240; Rathke, Ber. Dtsch. Chem. Ges. 18 (1885), 3102; Schiff, Justus Liebigs Ann. Chem. 148 (1868), 338; R. L. Frank, P. V. Smith, Org. Synth. III (1955), 735, N. B. Ambati et al., Synth. Commun. 27 (9). (1997), 1487-1493; W. O. Foye, J. Pharm. Sci. 66 (7) (1977), 923-926.

The resulting substituted thiourea derivative is then, in a second reaction step d), cyclized using a halogen-containing oxidizing agent, such as bromine, sulfuryl chloride or chlorine in an inert organic solvent, to give the substituted 2-aminobenzothiazole-5-carboxylic acid of the general formula IV-1a (in scheme 1, R³ is NH—CH₃). The cyclization is generally carried out in the range from −15 to +150° C., preferably in the range from 0 to 120° C. Suitable solvents are, in particular, the abovementioned aliphatic or cycloaliphatic hydrocarbons, the abovementioned aromatic hydrocarbons, the abovementioned anhydrous carboxylic acids, and furthermore C₁-C₄-alkanols, for example methanol, ethanol or isopropanol, dialkyl ethers, cyclic ethers and mixtures of the abovementioned solvents. For the oxidative cyclization of substituted thioureas to benzothiazoles see, for example, Houben-Weyl: “Methoden der organischen Chemie” V, Vol. E8B, 1994, p.865 f.

The substituted 2-aminobenzothiazole-5-carboxylic acid of the formula IV-1a can either be reacted directly in the abovementioned manner with a hydroxypyrazole of the formula III or an activated derivative thereof to give the compound I according to the invention (where Y=S and X=C—NH—R′″, where R″ is C₁-C₆-alkyl or unsubstituted or substituted phenyl).

If R³ in the formula IV-1a is NH—CH₃, it is also possible to prepare the o-aminothiobenzoic acids of the formula VIII (where R=R′=H) by hydrolysis according to step e). The hydrolysis is generally followed by the methylation to give the methyl thioether VIII (R=H, R′=CH₃). The hydrolysis in step e) is carried out, for example, by reacting the compound IV-1a (where R³=NH—CH₃) with an alkali metal hydroxide, for example lithium hydroxide, sodium hydroxide or potassium hydroxide, an alkaline earth metal hydroxide or an alkali metal iodide, such as sodium iodide, in a suitable solvent at elevated temperature, the reaction preferably being carried out in the absence of oxygen. Customary reaction temperatures are in the range from 0 to 200° C,. in particular in the range from 20 to 180° C. Suitable solvents are, in addition to the abovementioned aliphatic or cycloaliphatic hydrocarbons, the halogenated hydrocarbons, the aromatic hydrocarbons, the abovementioned ethers and alcohols, in particular aqueous monophasic systems and pyridine.

For the hydrolysis of the substituted 2-aminobenzothiazole-5-carboxylic acids see, for example: Organikum, 16th edition 1986, p. 415; Mc Murry, Org. React. 24 (1976), 187; Taschner et al., Rocz. Chem. 30 (1956), 323; Houben-Weyl: “Methoden der organischen Chemie”, Volume E8b, 1994; p. 1010 f.; J. Chem. Soc. Perkin Trans., Part 1, No. 12, (1976), 1291-1296, in particular A. R. Katritzky et al., J. Heterocycl. Chem. 30 (1) (1993), 135-139. The conversion into the methyl thioether VIII where R=H and R′=CH₃ succeeds in a simple manner by reacting with methyl iodide or dimethyl sulfate.

In a similar manner, it is possible to obtain compounds of the formula VIII where R=H by initially esterifying the 3-aminobenzoic acid of the formula Xa with a C₁-C₄-alkanol, for example with methanol, in a known manner. The resulting ester of the formula Xb (R=C₁-C₄-alkyl, in particular methyl) is then, in step f), reacted with isothiocyanic acid or a suitable salt of isothiocyanic acid, for example sodium isothiocyanate, in the presence of a concentrated mineral acid, to give the thiourea derivative. The reaction conditions correspond to the reaction conditions mentioned under step d) for the urea derivatives. The thiourea derivative is subsequently, in step g), cyclized under the abovementioned conditions to give the 2-aminobenzothiazole-5-carboxylic ester of the formula IV-1b (R³=NH₂). The resulting compound of the formula IV-1b where R³=NH₂ can be hydrolyzed in step e′ to give the compound VIII, which is subsequently, if appropriate, methylated (VIII: R=H, R′=CH₃).

It is also possible to convert the compound IV-1b in the manner described above into the compound,I according to the invention (where X=C—NH₂ and Y=S). Moreover, it is possible to initially diazotize the 2-amino group of the compound IV-1b and to introduce further functionalities into the 2-position of the benzothiazole skeleton in this way. The conversion of R³=NH₂ into R³=halogen is carried out in a known manner under Sandmeyer conditions. The conversion of R³=NH₂ into R³=H is carried out in a known manner by successive reaction of the 2-aminobenzothiazole-5-carboxylic ester with nitrite under acid conditions and then with a reducing agent, such as hypophosphoric acid, sodium borohydride, trialkylsilanes, trialkylstannanes, SnCl₂, NO, Wilkinson catalysts; see also J. Am. Chem. Soc. 71 (1949), p. 2137; J. Am. Chem. Soc. 72 (1950), p. 3013; 76 (1954) Vol. 76, p. 290.

A further route to the compounds of the formula VIII is shown in scheme 2.

Starting from 2,4-dicyanothioanisoles of the formula XI, in step h) the amide of the formula XII is prepared by selected hydrolysis. Owing to the different reactivity of the two methyl groups, the preparation succeeds under customary alkaline hydrolysis conditions, but the progress of the reaction is preferably monitored. Methods for the alkaline hydrolysis of nitriles are known, for example, from Org. Synth. Coll. Vol. 1, 1941, p. 321. In a further step i), the amide function in the compounds of the formula XII is then converted into an amino function by Hofmann degradation. This gives compounds of the formula VIII where R=H and R′=CH₃. Typical conditions for the Hofmann degradation are: aqueous alkaline chlorine or hypochloride solutions, temperatures in the range from 0 to 150° C., preferably in the range from 20 to 120° C. (see also Organikum, 16th edition 1986, p. 572).

A further route to benzothiazole-5-carboxylic acids is shown in scheme 3. This route utilizes the conversion of benzothiazoles of the formula XIV into the corresponding carboxylic acids, as shown in reaction step o).

The conversion of the bromobenzothiazole of the formula XIV into Fit the carboxylic acid of the formula IV-1 (R=H) is carried out, for example, by successive reaction of XIV with magnesium to give the corresponding Grignard compound and subsequent reaction of the Grignard compound with carbon dioxide. Alternatively, the compound XIV can be converted into the compound IV-1 by halogen-metal exchange using an alkali metal alkyl, for example a lithium alkyl, such as methyllithium, n-butyllithium or tert-butyllithium, and subsequent reaction of the reaction product with CO₂.

Reaction step o) in scheme 3 can also be realized by reacting the 5-bromobenzothiazole of the formula XIV with carbon monoxide, a base and water, under elevated pressure in the presence of a Pd, Ni, Co or Rh catalyst.

The catalysts nickel, cobalt, rhodium and in particular palladium can be present in metallic form or in the form of customary salts, such as in the form of halogen compounds, for example PdCl₂, RhCl₃.H₂O, acetates, for example Pd(OAc)₂, cyanides, etc., in the known valence states. Metal complexes with tertiary phosphines, metal alkylcarbonyls, metal carbonyls, e.g. CO₂(CO)₈, Ni(CO)₄, metal carbonyl complexes with tertiary phosphines, e.g. (PPh₃)₂Ni(CO)₂, or transition metal salts complexed with tertiary phosphines can also be present. The last-mentioned embodiment is preferred, in particular when the catalyst used is palladium. Here, the type of phosphine ligands is widely variable. They can be represented, for example, by the following formulae:

where n is the numbers 1, 2, 3 or 4 and the radicals R²⁴ to R²⁶ are low-molecular-weight alkyl, for example C₁-C₆-alkyl, aryl, C₁-C₄-alkylaryl, for example benzyl or phenethyl, or aryloxy. Aryl is, for example,. naphthyl, anthryl and preferably unsubstituted or substituted phenyl, where, with respect to the substituents, attention has to be paid only to their inertness to the carboxylation reaction, otherwise they can be widely varied and include all inert organocarbon radicals, such as C₁-C₆-alkyl radicals, for.example methyl, carboxyl radicals, such as COOH, COOM (M is, for example, an alkali metal, alkaline earth metal or ammonium salt), or organocarbon radicals attached via oxygen, such as C₁-C₆-alkoxy radicals.

The phosphine complexes can be prepared in a manner known per se, for example as described in the documents mentioned at the outset. For example, customary commercially available metal salts such as PdCl₂ or Pd(OCOCH₃)₂ are used as starting materials and the phosphine, for example P(C₆H₅)₃, P(n-C₄H₉)₃, PCH₃(C₆H₅)₂, 1,2-bis(diphenylphosphino)ethane, is added.

The amount,of phosphine, based on the transition metal, is usually from 0 to 20, in particular from 0.1 to 10, molar equivalents, particularly preferably from 1 to 5 molar equivalents.

The amount of transition metal is not critical. Of course, for reasons of cost,. preference is given to using a relatively small amount, for example from 0.1 to 10 mol %, in particular from 1 to mol %, based on the starting material IV.

For preparing the benzothiazole-5-carboxylic acids IV-1 (R=OH), the reaction is carried out with carbon monoxide and at least equimolar amounts of water, based on the starting materials XIV. The reaction component water can simultaneously also serve as solvent, i.e. the maximum amount is not critical.

However, depending on the nature of the starting materials and the catalysts used, it may also be advantageous for the solvent used to be, instead of the reaction component, another inert solvent or the base which is used for the carboxylation.

Suitable inert solvents for carboxylation reactions are customary solvents such as hydrocarbons, for example toluene, xylene, hexane, pentane, cyclohexane, ethers, for example methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, substituted amides, such as dimethylformamide, persubstituted ureas, such as tetra-C₁-C₄-alkylureas, or nitrites, such as benzonitrile or acetonitrile.

In a preferred embodiment of the process, one of the reaction components, in particular the base, is used in an excess, so that no additional solvent is necessary.

Bases which are suitable for the process are all inert bases which are able to bind hydrogen iodide or hydrogen bromide liberated during the reaction. Examples which may be mentioned here are tertiary amines, such as tert-alkylamines, trialkylamines, such as triethylamine, cyclic amines, such as N-methylpiperidine or N,N′-dimethylpiperazine, pyridine, alkali metal carbonates or bicarbonates, or tetraalkyl-substituted urea derivatives, such as tetra-C₁-C₄-alkylurea, for example tetramethylurea.

The amount of base is not critical, customarily from 1 to 10, in particular from 1 tb 5, mol are used. When the base is simultaneously used as solvent, the amount is generally such that the reaction components are dissolved, unnecessarily high excesses being avoided for reasons of practicability in order to save costs, to be able to employ small reaction vessels and to ensure that the reaction components have maximum contact.

During the reaction, the carbon monoxide pressure is adjusted such that an excess of CO, based on XIV, is always present. At room temperature, the carbon monoxide pressure is preferably from 1 to 250 bar, in particular from 5 to 150 bar, of CO.

The carbonylation is generally carried out continuously or batchwise at from 20 to 250° C., in particular from 30 to 150° C. In the case of batchwise operation, carbon monoxide is advantageously continuously injected onto the reaction mixture to maintain a constant pressure.

The 5-bromobenzothiazoles XIV used as starting materials are known or can easily be prepared by suitable combination of known syntheses and according to the reaction sequence described in scheme 3.

According to scheme 3, it is possible, for example, to convert o-chloronitrobenzenes of the formula XIII into the corresponding o-nitrothioethers using alkali metal salts of alkylmercaptans (step k). The resulting thioether can be brominated selectively in the 3-position with respect to the nitro group (step 1). Brominating reagents which are customarily used for this purpose are, in addition to bromine—if appropriate in combination with a Lewis acid such as FeBr₃—, also N-bromosuccinimide, N-bromohydantoin and pyridinium perbromide. The bromination is preferably carried out in an organic solvent, for example an aliphatic or cycloaliphatic hydrocarbon, halogenated hydrocarbon or anhydrous organic acids, at temperatures in the range from −15 to 150° C., preferably in the range from −15 to 100° C. (see, for example, Organikum, 16th edition, 1985, p. 315). Subsequently, in step m), the nitro group is reduced to the amino group. The conditions for step m) correspond to the conditions given for step c) in scheme 1. The o-aminothioether from step m) is subsequently, in step n), cyclized to the 5-bromobenzothiazole XIV. The reaction conditions required for this step correspond to the conditions given for step a) in scheme 1.

For preparing the benzothiazole S-dioxide compounds of the formula I (Y=SO₂), for example, the benzothiazole-5-carboxylic acids IV-1a or IV-1b or the 5-bromobenzothiazole-5-carboxylic acids XIV are reacted with an oxidizing agent giving the corresponding S-dioxide, which is then processed further as described to give the target compound of the formula I where Y=SO₂. However, preference is given to initially oxidizing the thiomethyl ether of the formula VIII (scheme 1, formula VIII where R=H and R′=CH₃) to give the S-dioxide VIIIc, which is subsequently cyclized to give the benzothiazole S-dioxide 5-carboxylic acid of the formula IV-1c.

The oxidation of VIII to the S-dioxide is carried out using oxidizing agents,.such as peroxy acids, for example m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, or using hydrogen peroxide, which is preferably employed together with a transition metal catalyst, for example sodium tungstate (VI). The cyclization of o-methylsulfonylaminobenzenes of formula VIIIc is carried out analogously to the method described in Chem. Heterocycl. Comp. Vol.3, 1967, p.197 ff.

A synthesis of benzoxazole-5-carboxylic ester derivatives of the formula IV-2 (X=C—R³, Y=O) is described in scheme 4. Here, starting from 3-nitrotoluenes of the formula IX, a 3-aminobenzoic ester of the formula Xb (R=C₁-C₄-alkyl) is initially prepared in the manner described for scheme 1. In step p), the amino group in Xb is first diazotized in a known manner, and the product is subsequently reacted with alkali metal azides to give the corresponding 3-azidobenzoic acids of the formula XV. The azide XV is then, in reaction step q), reacted with an alkanecarboxylic acid, which may also be halogenated, for example formic acid, acetic acid, trifluoroacetic acid or propionic acid, to give the benzoxazole-5-carboxylic ester of the formula IV-2a (R³=C₁-C₄-alkyl). The compound IV-2a can either be reacted directly to give the pyrazolyl derivative of the formula I according to the invention where X=CR³ and Y=O or, alternatively, be hydrolyzed in reaction step r) to give the o-aminophenol of the formula XVI. Like the o-aminothiophenols of the formula VIII, the compounds XVI can then be converted into benzoxazole-5-carboxylic esters of the formula IV-2.

In reaction step p), initially an aromatic diazonium compound is prepared from the amine of the formula Xb, in aqueous acidic solution or in an anhydrous acid, such as formic acid, acetic acid or trifluoroacetic acid, using an inorganic nitrite, such as sodium nitrite, or an organic nitrite, such as isoamyl nitrite. An alkali metal azide, for example sodium azide, is then added to the solution or suspension of the diazonium compound, giving the 3-azidobenzoic ester according to scheme 4. The reaction temperature for the reaction is generally in the range from −15 to +50° C., preferably in the range from 0 to 20° C. See also K. G. Pinney et al., J. Org. Chem. [JOCEAH] 56 (9) (1991), 3125-3133.

Reaction step q) is preferably carried out in the anhydrous acid HOOC—R³ which is desired for the condensation, in an aromatic hydrocarbon, such as benzene, toluene, xylene or chlorobenzene. The reaction temperature is generally in the range from 0 to 150° C. and preferably in the range from 50 to 145° C. (See also B. Decroix et al., Bull. Soc. Chim. Fr. 1976, 621; S. Chaudhury et al., Can. J. Chem. 60 (1982), 1122). The hydrolysis of the benzoxazole-5-carboxylic ester obtained in step q) to give the 3-amino-4-hydroxybenzoic ester of the formula XVI is carried out, for example, under the conditions given for reaction step e) in scheme 1. The condensation of compound XVI to the benzoxazole-5-carboxylic ester in step 8) is carried out, for examples under the reaction conditions given for step a) in scheme 1. (For step s), see also Houben-Weyl, “Methoden der organischen Chemie”, Vol. E8a, 1993, p. 1020 f.)

Another route to the benzoxazole-5-carboxylic acids of the formula IV (X=C—R³, Y=O) is shown in scheme 5.

Here, an o-chloronitrobenzene of the formula XIII is initially converted by nucleophilic exchange of halogen for methoxy into an o-nitroanisole (step t)). This is then brominated under the reaction conditions given for step 1) in scheme 3, the bromine atom being introduced selectively into the p position to the methoxy group. The brominated nitroanisole is then initially reduced selectively to give the amino compound, and the hydroxyl function is subsequently released by ether cleavage. This gives 2-amino-4-bromophenols. These are then cyclized to the 5-bromobenzoxazole of the formula XVII under the reaction conditions given for step s). Compound XVII is then reacted under the reaction conditions described for step o) in scheme 3 to give the benzoxazole-5-carboyxlic acid of the formula IV (X=C—R³ and Y=O).

A process for preparing benzimidazole-5-carboxylic esters is shown in scheme 6.

Once more, 3-nitrotoluenes are used as starting materials here, and they are converted in the manner described above into 3-aminobenzoic esters of the formula Xb. The compounds Xb are then, in reaction step y), reacted with a carboxylic acid of the formula R³—CO₂H or a reactive carboxylic acid equivaent RCOL¹, where L¹ is as defined above, to give a carboxamide of the formula XVIII. Here, R³ has one of the meanings given above. XVIII is then converted under acidic conditions, for example with phosgene or phosphoryl chloride, into a nitrilium ion, which is quenched with an amine of the formula R⁴—NH₂ or ammonia, resulting in an imino amide of the formula XIX. The compound XIX can then be converted under oxidizing conditions, as described, for example, for reaction step b) or g) in scheme 1, into the benzimidazole-5-carboxylic esters, which for its part can be hydrolyzed with the carboxylic acid.

Step y) is generally carried out under the customary reaction conditions for forming amides from carboxylic acids or carboxylic acid derivatives and aromatic amines. The reaction temperature is generally in the range from −15 to 200° C., preferably in the range from 20 to 150° C.

For preparing the imino amide of the formula XIX, the amide of the formula XVIII is initially dissolved under exclusion of water in an organic solvent, for example one of the abovementioned cycloaliphatic or aromatic hydrocarbons or an ether, and converted into the nitrilium ion using an inorganic acid, for example hydrochloric acid, or sulfuric acid, a Lewis acid, such as titanium tetrachloride, or an acid chloride, such as sulfonyl chloride, sulfuryl chloride, phosphoryl chloride or phosgene. The required temperatures are generally in the range from −15 to 150° C. and preferably in the range from 20 to 140° C. The nitrilium ion is then quenched with ammonia or an amine of the formula R⁴—NH₂.

The cyclization of the compound XIX to the benzimidazole-5-carboxylic ester of the formula IV (X=C—R³, Y=C-R⁴) is generally carried out using an oxidizing agent, such as lead tetraacetate, thallium(III) nitrite, sulfuryl chloride or sodium hypochlorite, under anhydrous conditions. Suitable solvents are, for example, aliphatic or cycloaliphatic hydrocarbons, aromatic hydrocarbons or ethers. The reaction is generally carried out at temperatures in the range from −15 to +150° C. and preferably in the range from 0 to 140° C. For the preparation of benzimidazoles from iminoamides see also (Can. J. Chem. 60 (1982), p.1122).

Benzoisothiodiazoles of the formula IV-4 (X—Y=S═N) are prepared, for example, starting from benzimidazole-5-carboxylic acids or their esters, in the manner described in scheme 7.

In this case a benzimidazolecarboxylic ester or the free carboxylic acid is initially hydrolyzed to 3,4-diaminobenzoic acid. This is subsequently cyclized with sulfurous acid or its derivatives, for example SO₂ or SO₂Cl₂, to give the benzoisothiadiazole-5-carboxylic acid of the formula IV-4. The cyclization is usually carried out at from 0 to 200° C. and preferably at from 50 to 150° C., for example in a solvent or in the melt (see also: Chem. Ber. 100 (1967), 2164).

Benzothiadiazole-5-carboxylic acids of the formula IV-5 (X=N, Y=S) can be prepared starting from 2-aminothiophenol-5-carboxylic acids of the formula VIII (R═R′=H). To this end, the compounds of the formula VIII are initially diazotized, for example by reaction with organic or inorganic nitrite in an aqueous neutral reaction medium at temperatures in the range from −15 to +20° C. The aqueous solution or suspension of the diazonium salt is subsequently acidified, whereupon the compound of the formula IV-5 forms. This can then be obtained in a conventional manner from the reaction mixture, for example by extraction with an organic solvent. The preparation of the starting materials III is described in scheme 1. The benzothiadiazolecarboxylic acids IV-5 (X=N, Y=S) can be prepared, for example analogously to the process described in U.S. Pat. No. 5,770,758.

EXAMPLES 4-[4′-Methylbenzothiazol-5′-ylcarbonyl]-5-hydroxy-1-methylpyrazole (Example 1)

With heating, 189 g (1 mol) of 2-methyl-3-cyano-4-thiocyanoaniline were dissolved in 1 kg of glacial acetic acid, and 400 g (4 mol) of conc. HCl and, after 15 min of stirring, 400 ml of water were then added such that a finely divided suspension of the hydrochloride was formed. After brief stirring (15 to 30 min), a solution of 69 g (1 mol) of sodium nitrite in 140 ml of water was slowly added dropwise at from −5 to 0° C. In a separate stirred flask, 245 g (5 mol) of NaCN were dissolved in a mixture of.1.5 1 of water and 136 g (2 mol) of a 25 percent solution of ammonia and water, and 250 g (1 mol) of CuSO₄.5H₂O were then added. At 25° C., a diazonium solution, which had been prepared beforehand and was kept at 0° C., was then rapidly added dropwise to the Cu complex, the temperature not exceeding 40° C. After the evolution of gas had ceased, stirring was continued for 30 min. The precipitated solid was filtered off with suction and washed three times with water. The filtrate was extracted with 2 l of methylene chloride. The solid was then added to a stirred vessel and admixed with 1 l of conc. HCl. The methylene chloride extract was subsequently added, and the mixture was stirred for 15 min. The organic phase was separated off, undissolved fractions were filtered off and the organic phase was then washed three times with water and, after drying over sodium sulfate, concentrated. To remove undesirable components, the crude product was dissolved in ethyl acetate, undissolved particles were filtered off and the solution was then concentrated.

Yield: 170 g (85%). M.p.: 95-107° C.

1.2 3-Methyl-2,4-dicyanothiophenol

At 25-35° C., a solution of 110.5 g (0.85 mol) of 60 percent pure sodium sulfide in 425 ml of water was added dropwise to a solution of 170 g (0.85 mol) of 2-methyl-4-thiocyanoisophthalonitrile in 850 ml of methanol, and the mixture was stirred at room temperature for 3 hours. The mixture was then admixed with 1000 ml of water and extracted with methyl tert-butyl ether. The aqueous phase was acidified to pH 1 using HCl, and the thiophenol was extracted with methylene chloride. The extract was washed three times with water, and the organic phase was then separated off, dried over sodium sulfate and concentrated. Yield: 150 g (99%).

M.p.: 172-179° C.

1.3 3-Methyl-2,4-dicyanothioanisole

50 g (0.29 mol) of 3-methyl-2,4-dicyanothiophenol were added to a solution of 23 g (0.58 mol) of NaOH in 400 ml of water, and 73 g (0.58 mol) of dimethyl sulfate were then added dropwise at 25-35° C. The mixture was stirred at 25° C. for 16 h, after which a solid had precipitated out, which was filtered off with suction, washed twice with water and then recrystallized from glacial acetic acid/water. Yield: 43 g (80%).

M.p.: 176-181° C.

1.4 2-Methyl-3-aminocarbonyl-4-methylsulfanylbenzoic Acid

34 g (0.181 mol) of 3-methyl-2,4-dicyanothioanisole were suspended in a solution of 21.7 g (0.54 mol) of NaOH in 200 ml of water, and the mixture was heated at the boil for 8 h. After cooling, some of the product precipitated out and was isolated by filtration with suction and washing with water. The still alkaline filtrate was extracted with MTBE, and the extract was discarded. The aqueous phase was acidified with conc. HCl (pH 1) and extracted with ethyl acetate. Yield: 29 g (71%).

M.p.: 230-240° C.

1.5 3-Amino-2-methyl-4-methylsulfanylbenzoic Acid

a) From 2-Methyl-3-aminocarbonyl-4-methylsulfanylbenzoic Acid

At, 0° C., 2.9 g of bromine (0.018 mol) were added dropwise to a solution of 3.64 g (0.09 mol) of NaOH in 40 ml of water. 4.1 g (0.018 mol) of 2-methyl-3-aminocarbonyl-4-methylsulfanylbenzoic acid were then added a little at a time at 0° C. The mixture was stirred at 0° C. for 1 h and then warmed to 20° C. The reaction mixture was subsequently acidified using 10% strength HCl and extracted with ethyl acetate. The resulting precipitate was repeatedly suspended in ethyl acetate and dried. Yield: 0.95 g (27%).

b) From Methyl 2-Amino-4-methylbenzothiazole-5-carboxylate

10 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.045 mol.) were dissolved in a mixture of 120 ml of water, 120 ml of ethylene glycol and 50 g of NaOH, and the mixture was stirred at 130° C. for 20 h. The mixture was then diluted with 50 g of ice, 3 drops of (n-Bu)₄N+OH— solution were added and finally, at 20° C., 6.25 ml of dimethyl sulfate (0.05 mol) in 15 ml of toluene were added dropwise. After 30 min, the mixture was acidified with conc. HCl and the precipitate was filtered off with suction, washed with water and dried.

Yield: 7 g (71%). M.p.: 225° C. (decomp.)

1.6 Methyl 3-Amino-2-methyl-4-methylsulfanylbenzoate

2 g of 3-amino-2-methyl-4-methylsulfanylbenzoic acid (0.01 mol) were dissolved in 20 ml of methanol and admixed with 2.0 g of conc. sulfuric acid, and the mixture was heated at 60° C. for 2 h. After cooling, the reaction mixture was poured into water, neutralized and extracted with ethyl acetate. After washing and drying, the solvent was removed.

Yield: 1.3 g (62%). M.p.: 98-103° C.

1.7 Methyl 3-Formamidyl-2-methyl-4-methylsulfanylbenzoate

At 40° C., 4.75 g of methyl 3-amino-2-methyl-4-methylsulfanylbenzoate (0.05 mol) were added a little at a time to a mixture of 30 ml of acetic anhydride and 2.2 g of formic acid (0.05 mol). After 5 h, the solution was allowed to cool and poured into ice-water, and the mixture was extracted exhaustively with methylene chloride. The organic phases were washed and dried, and the solvent was subsequently removed. Yield: 4.7 g (0.044 mol).

M.p.: 170-176° C.

1.8 Methyl 4-Methylbenzothiazole-5-carboxylate

a) From Methyl 3-Formamidyl-2-methyl-4-methylsulfanylbenzoate

2.4 g of methyl 3-formamidyl-2-methyl-4-methylsulfanylbenzoate (0.01 mol) were dissolved in methylene chloride. The mixture was saturated with phosgene gas, and excess phosgene was subsequently flushed out with nitrogen. 1.5 g of triethylamine were then added dropwise. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate, the salt was filtered off and the organic phase was reconcentrated. The residue was purified by silica gel column chromatography. Yield: 1.6 g (77%).

b) From Methyl 2-Amino-4-methylbenzothiazole-5-carboxylate

15 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.07 mol) were initially charged in 450 ml of phosphoric acid, and the mixture was cooled to −8° C. 27.9 g of NaNO₂ (0.4 mol) in 30 ml of water were then added dropwise such that the temperature did not exceed −4° C. The diazonium salt was then added dropwise, at 5-10° C., to 169 ml of hypophosphoric acid, and the mixture was stirred at 20° C. overnight. The reaction solution was then neutralized and extracted exhaustively with ethyl acetate. The organic phases Age were washed and dried and the solvent was then removed.

Yield: 6.84 g (49%). M.p.: 90-92° C.

1.9 4-Methylbenzothiazole-5-carboxylic Acid

16.6 g of methyl 4-methylbenzothiazole-5-carboxylate (0.08 mol) were dissolved in 280 ml of 5% strength aqueous potassium hydroxide solution and heated at reflux for 2.5 h. After cooling, the mixture was acidified using phosphoric acid. The product was filtered off and subsequently dried.

Yield: 14.34 g (93%). M.p.: 260-265° C.

1.10 1-Methylpyrazol-5-yl 4-Methylbenzothiazole-5-carboxylate

0.65 g of 4-methylbenzothiazole-5-carboxylic acid (0.004 mol) and 0.33 g of 1-methyl-5-hydroxypyrazole (0.004 mol) were dissolved in 30 ml of abs. acetonitrile and admixed with 0.65 g of EDC (0.004 mol), 0.5 ml of triethylamine and a catalytical amount of DMAP. After the reaction had ended, the solution was poured into water and extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by silica gel column chromatography. Yield: 0.42 g (41%).

¹H NMR (CDCl₃, TMS): δ=3.18 (s, 3H); 3.83 (s, 3H); 6.24 (d, 1H); 7.49 (d, 1H); 7.94 (d, 1H); 8.21 (d, 1H); 9.08 (s, 1H); ppm. EDC=ethyl-(3′-dimethylaminopropyl)carbodiimide DMAP=4-dimethylaminopyridine

1.11 4-(4′-Methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole

0.38 g of 1-methylpyrazol-5-yl 4-methylbenzothiazole-5-carboxylate (1.39 mmol) was dissolved in 25 ml of dioxane, and the mixture was admixed with 0.28 g of K₂CO₃ (2 mmol). The mixture was refluxed until the reaction had gone to completion, the solvent was removed under reduced pressure and the residue was taken up in water. The aqueous phase was extracted with methylene chloride, adjusted to pH 2 and extracted with ethyl acetate. The solvent was removed and the product was then purified by trituration. Yield: 0.25 g (66%).

M.p.: 149-150° C.

4-(2′-Chloro-4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 2)

2.1 Methyl 3-Amino-2-methylbenzoate

210 g of methyl 2-methyl-3-nitrobenzoate (1.08 mol) were dissolved in 4 l of methanol, 21 g of Pd/C were added and the mixture was subsequently hydrogenated at ambient pressure. After the reaction had ended, the catalyst was filtered off and the solvent was removed. Yield: 178 g (quant.).

¹H NMR (CDCl₃, TMS): δ=2.34 (s, 3H); 3.60 (s, brd, 2H, NH₂); 3.84 (s, 3H); 6.80 (d, 1H); 7.04 (dd, 1H); 7.21 (d, 1H) ppm.

2.2 N-(2-Methyl-3-methoxycarbonylphenyl)thiourea

90.7 g of methyl 3-amino-2-methylbenzoate (0.55 mol) were dissolved in 510 ml of chlorobenzene and, at −5° C., admixed with 14 ml of conc. sulfuric acid and 49 g of sodium thiocyanate (0.6 mol). 2 ml of 15-crown-5 were then added, and the reaction mixture was heated at 100° C. for 13 h. After cooling, the solid was filtered off with.suction, washed with water and dried. Yield: 104.8 g (85%).

M.p.: 198° C.

2.3 Methyl 2-Amino-4-methylbenzothiazole-5-carboxylate

56 g of N-(2-methyl-3-methoxycarbonylphenyl)thiourea (0.25 mol) were dissolved in 2 l of chlorobenzene, and the mixture was cooled to 0° C. 40 g of bromine (0.25 mol) in 100 ml of chlorobenzene were then added dropwise. The reaction mixture was heated at 90° C. for 3 h, and the precipitate was filtered off with suction and washed with methylene chloride. The precipitate was then dissolved in ethyl acetate and extracted with sodium bicarbonate solution. After washing and drying, the product was obtained by stripping off the solvent. Yield: 43 g (80%).

M.p.: 220° C.

2.4 Methyl 2-chloro-4-methylbenzothiazole-5-carboxylate

At −8° C., a solution of 9.3 g of NaNO₂ (0.14 mol) in 10 ml of water was added dropwise to a solution of 5 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.02 mol) in 150 ml of phosphoric acid. At 5° C., a solution of 3 g of CuCl and 12 ml of conc. HCl was then added dropwise. The reaction mixture was heated to 100° C. After cooling, the residue was filtered off with suction, washed with water and dried. The product was purified by silica gel column chromatography.

Yield: 3 g (55%). ¹H NMR (CDCl₃, TMS) δ=2.98 (s, 3H); 3.95 (s, 3H); 7.67 (d, 1H); 7.95 (d, 1H) ppm.

2.5 2-Chloro-4-methylbenzothiazole-5-carboxylic Acid

3 g of methyl 2-chloro-4-methylbenzothiazole-5-carboxylate (0.012 mol). were dissolved in 50 ml of THF, and the mixture was cooled to 0° C. and admixed with a solution of 0.6 g of LiOH in 20 ml of water. After 1 h, the mixture was allowed to warm to 20° C., and stirring was continued for another 20 h. The solvent was then removed-under reduced pressure, and the aqueous phase was acidified with phosphoric acid and extracted with ethyl acetate. The extract was washed and dried and the solvent was stripped off to give the product.

Yield: 2.6 g (92%). M.p.: >250° C. ¹H NMR (D₆-DMSO, TMS) δ=2.85 (s, 3H); 7.90 (d, 1H); 8.02 (d, 1H) ppm.

2.6 1-Methylpyrazol-5-yl 3-Chloro-4-methylbenzothiazole-5-carboxylate

1 g of 3-chloro-4-methylbenzothiazol-5-carboxylic acid (4.4 mol) and 0.46 g of 1-methyl-5-hydroxypyrazole (4.7 mol) were dissolved in 50 ml of abs. acetonitrile and admixed with 1 g of EDC, 0.7 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the product was extracted with ethyl acetate. The organic phase was washed and dried and the product was purified by crystallization/column chromatography. Yield: 0.22 g (16%).

¹H NMR (CDCl₃, TMS) δ=3.08 (s, 3H); 3.80 (s, 3H); 6.25 (s, 1H); 7.46 (s, 1H); 7.77 (d, 1H); 8.17 (d, 1H) ppm.

2.7 4-(3′-Chloro-4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole

0.22 g of 1-methylpyrazole-5-yl 3-chloro-4-methylbenzothiazole-5-carboxylate (0.7 mol) was dissolved in 35 ml of dioxane and admixed with 0.5 g of K₂CO₃. The mixture was refluxed until the reaction had gone to completion, the solvent was removed under reduced pressure and the residue was taken up in water. The aqueous phase was extracted with methylene chloride, adjusted to pH 2 and extracted with ethyl acetate. The solvent was removed and the product was then purified by trituration. Yield: 0.19 g (86%).

¹H NMR (CDCl₃, TMS) δ=2.82 (s, 3H); 3.76 (s, 3H); 7.40 (s, 1H); 7.52 (d, 1H); 7.73 (d, 1H) ppm.

4-(4′-Methylbenzothiadiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 3)

3.1 4-Methylbenzothiadiazole-5-carboxylic Acid

5 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.02 mol) in 28.6 g of 50% strength KOH were stirred at 120° C. for 4 h. The mixture was then neutralized with 10% strength HCl and admixed with an excess of 40% strength NaNO₂ solution at 0-10° C. The reaction mixture was acidified and extracted with ethyl acetate. The extract was washed and dried, and the product was obtained by stripping off the solvent. Yield: 1.3 g (28%).

3.2 4-(4′-Methylbenzothiadiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole

1.3 g of 4-methylbenzothiadiazole-5-carboxylic acid (6.3 mmol) and 0.65 g of 1-methyl-5-hydroxypyrazole (6.6 mmol) were dissolved in 50 ml of abs. acetonitrile and admixed with 1.4 g of EDC (7.5 mmol), 1 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the product was extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by silica gel column chromatography. Yield: 0.7 g (39%).

M.p.: 152-153° C.

3.3 4-(4′-Methylbenzothiadiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole

0,7 g of 1-methylpyrazol-5-yl 4-methylbenzothiadiazole-5-carboxylate (2.4 mmol) was dissolved in 40 ml of dioxane and admixed with 0.5 g of K₂CO₃. The mixture was refluxed until the reaction had gone to completion, the solvent was removed under reduced pressure and the residue was taken up in water. The aqueous phase was extracted with methylene chloride, adjusted to pH 2 and extracted with ethyl acetate. The solvent was removed and the product was then purified by trituration. Yield: 0.65 g (93%).

M.p.: 207-209° C.

4-(2′-Methylamino-4′-methylbenzothiazole-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 4)

4.1 2-Methylamino-4-methylbenzothiazole-5-carboxylic Acid

99 g of 3-amino-2-methylbenzoic acid (0.655 mol) were initially charged in 500 ml of acetic acid and, at 80° C,. admixed with 51 g of methyl isothiocyanate (7 mol) in 100 ml of acetic acid. After 2 h, 106 g of bromine (0.66 mol) in 20 ml of acetic acid were added dropwise at 50° C. The mixture was subsequently heated at about 100° C. for 2 h and, after the reaction had ended, allowed to cool. The precipitate was filtered off, the filtrate was concentrated to about 50 ml and the remaining filtrate and the precipitate were added to water. The aqueous phase was adjusted to pH 5 and the precipitate was filtered off at 8° C. It was subsequently washed with water and dried. Yield: 66 g (42%).

¹H NMR (D₆-DMSO, TMS) δ=2.72 (s, 3H); 2.95 (d, 3H); 7.46 (d, 1H); 7.57 (d, 1H); 8.04 (q, 1H, NH) ppm.

4.2 1-Methylpyrazol-5-yl 2-Methylamino-4-methylbenzothiazole-5-carboxylate

3.1 g of 2-methylamino-4-methylbenzothiazole-5-carboxylic acid (0.014 mol) and 1.4 g of 1-methyl-5-hydroxypyrazole (0.015 mol) were dissolved in 110 ml of abs. acetonitrile and admixed with 2.67 g of EDC (0.014 mol), 1,2 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the mixture was extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by crystallization. Yield: 2.2 g (52%).

¹H NMR (D₆-DMSO): δ=2.80 (s, 3H); 3.00 (d, 3H); 3.73 (s, 3H); 6.22 (d, 1H); 7.43 (d, 1H); 7.72 (d, 1H); 7.84 (d, 1H); 8.20 (s, brd, 1H) ppm.

4-(1′-Methylbenzotriazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 5)

5.1 1-Methylpyrazol-5-yl 1-Methylbenzotriazole-5-carboxylate

1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 0.87 g of 1-methyl-5-hydroxypyrazole (8.9 mmol) were dissolved in 70 ml of abs. acetonitrile and admixed with 1.62 g of EDC (8.5 mmol), 2 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the mixture was extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by crystallization. Yield: 0.77 g (35%).

¹H NMR (CDCl₃, TMS): δ=3.82 (s, 3H); 4.40 (s, 3H); 6.28 (d, 1H); 7.48 (d, 1H); 7.67 (d, 1H); 8.36 (d, 1H); 8.98 (s, 1H) ppm.

5.2 4-(1′-Methylbenzotriazol-5-ylcarbonyl)-5-hydroxy-1-methylpyrazole

0.53 g of 1-methylpyrazol-5-yl 1-methylbenzotriazole-5-carboxylate (2 mmol) was dissolved in 30 ml of dioxane and admixed with 0.43 g of K₂CO₃ (3 mmol). The mixture was refluxed until the reaction had gone to completion, the solvent was removed under reduced pressure and the residue was taken up in water. The aqueous phase was extracted with methylene chloride, adjusted to pH 2 and extracted with ethyl acetate. The solvent was removed and the product was then purified by trituration. Yield: 0.31 g (58%).

¹H NMR (CDCl₃, TMS): δ=3.78 (s, 3H); 4.39 (s, 3H); 4.75 (s, brd, 1H); 7.63 (d, 1H); 7.86 (s, 1H); 8.08 (d, 1H); 8.56 (s, 1H) ppm.

6. 4-(4′-Methylbenzothiazol-5′-ylcarbonyl)-5-methoxy-1-methylpyrazole (Example 6)

At room temperature, 0.26 g of iodomethane was added dropwise to a mixture of 0.3 g of 4-(4′-methylbenzothiazol-5′-yl-carbonyl)-5-hydroxy-1-methylpyrazole from Example 1 and 0.18 g of potassium carbonate in 15 ml of dimethylformamide. The mixture was stirred at 50° C. for 75 min and at room temperature overnight. For work-up, the reaction mixture was poured into water and extracted with methyl tert-butyl ether. Washing and drying of the combined organic phases and removal of the solvent gave the compound I-1e.394 in the form of whitish-yellow crystals. Yield: 0.15 g (48%).

M.p.: 138-141° C.

In an analogous manner, the compound of Example 13 (I-1g.394) was prepared by reacting the compound I-1a.394 from Example 1 with benzyl bromide, and the compounds I-1i.394 (Example 16), I-1u.394 (Example 15) and I-1v.394 (Example 18) were prepared by reaction with the respective acid chloride.

The compounds of Example 7 to 12, 14, 17 and 19 to 52 were prepared analogously to the sequence described in Example 1, steps 1.10 and 1.11, by reacting the respective carboxylic acid IVb with the appropriate 5-hydroxypyrazole III.

M.p. [° C.] or Ex. Structure/Compound No. ¹H-NMR [ppm] 1

149-150° C. I-1a.394 2

135-137° C. I-1a.396 3

207-209° C. I-4a.2 4

I-1a.447 5

CDCl₃, TMS: 3.78(s, 3H), 4.39(s, 3H), 4.75(OH), 7.63(d, 1H), 7.86(s, 1H), 8.08(d, 1H), 8.56(s, 1H) ppm. I-4a.38 6

138-141° C. I-1e.394 7

141-143° C. I-4c.2 8

122-125° C. I-4d.2 9

118-122° C. I-1c.396 10

CDCl₃, TMS: 2.6(s, 3H), 3.78(s, 3H), 5.5(OH), 7.2-7.38(m, 3H), 7.4-7.55 (m, 3H), 7.6(d, 1H) ppm. I-1a.790 11

CDCl₃, TMS: 1.55(d,6H), 2.62(s, 3H), 4.6(m, 1H) 5,5(OH), 7.2-7.38(m, 3H), 7.4-7.55(m, 3H), 7.6(d, 1H) ppm. I-1c.790 12

135-137° C. I-1c.394 13

CDCl₃, TMS: 2.81(s, 3H), 3.79(s, 3H), 5.2(s, 2H) 7.08(d, 1H), 7.2-7.45(m, 6H), 7.65(d, 1H), 9.1(s, 1H) ppm. I-1g.394 14

148-152° C. I-1a.405 15

CDCl₃, TMS: 2.78(s, 3H), 3.78(s, 3H), 7.25-7.55(m, 4H), 7.65(d, 1H), 7.8-7.9(m, 3H), 8.9(s, 1H) ppm. I-1u.394 16

CDCl₃, TMS: 2.78(s, 3H), 3.78(s, 3H), 7.2-7.38(m, 3H), 7.58(d, 1H), 7.67-7.78(m, 2H), 7.82(s, 1H), 8.99(s, 1H) ppm. I-1i.394 17

 98-101° C. I-1d.394 18

CDCl₃, TMS: 0.8(m, 2H), 1.05(m, 2H), 1.66(m, 1H), 2.8(s, 3H), 3.75(s, 3H), 5,6(OH), 7.45(d, 1H), 7.8(s, 1H), 7.82(d, 1H), 9.03(s, 1H) ppm. I-1v.394 19

145-148° C. I-1c.412 20

CDCl₃, TMS: 1.58(d, 6H), 2.90(s, 3H), 4.62(m, 1H), 7.2(m, 2H), 7.48(s, 1H), 7.54(d, 1H), 7.8(d, 1H), 8.14(m, 2H) ppm. I-1c.457 21

CDCl₃, TMS: 1.56(d, 6H), 2.92(s, 3H), 3.9(s, 3H), 4.62(m, 1H), 7.02(d, 2H), 7.46(s, 1H), 7.5(d, 1H), 7.80(d, 1H), 8.08(d, 2H) ppm. I-1c.466 22

CDCl₃, TMS: 1.72(s, 3H), 2.88(s, 3H), 3.64(s, 3H), 3.88(s, 3H), 7.0(m, 2H), 7.22(d, 1H), 7.78(d, 1H), 8.06(d, 2H) ppm. I-1m.466 23

204-205° C. I-1a.466 24

CDCl₃, TMS: 1.64(s, 9H), 2.92(s, 3H), 7.20(m, 2H), 7.48(s, 1H), 7.62(d, 1H), 7.82(d, 1H), 8.16(m, 2H) ppm. I-1d.457 25

127-128° C. I-1c.456 26

123-127° C. I-1m.456 27

153-154° C. I-1d.456 28

CDCl₃, TMS: 2.78(s, 3H), 3.78(s, 3H), 3.88(s, 3H), 7.0-7.12(m, 2H), 7.2-7.4(m, 4H), 7.46(d, 1H), 8.85(OH) ppm. I-1a.802 29

CDCl₃, TMS: 1.61(d, 6H), 2.80(s, 3H), 3.90(s, 3H), 4.63(m, 1H), 7.0-7.12(m, 2H), 7.25-7.48(m, 4H), 7.55(d, 1H), 8.95(OH) ppm. I-1c.802 30

134-137° C. I-2a.406 31

CDCl₃, TMS: 1.53(t, 3H), 1.55(d, 6H), 2.78(s, 3H), 3.03(q, 2H), 4.62(m, 1H), 738(d, 1H), 7.42(s, 1H), 7.53(d, 1H) ppm. I-2c.406 32

102-105° C. I-1c.408 33

107-110° C. I-1c.405 34

CDCl₃, TMS: 2.82(s, 3H), 3.58(s, 3H), 3.70(s, 3H), 4.88(s, 2H); 742(s, 1H), 7.52(d, 1H), 7.82(d, 1H), 7.90(OH) ppm. I-1a.420 35

197-200° C. I-1d.475 36

100-104° C. I-1c.420 37

108-112° C. I-1a.418 38

 84-87° C. I-1c.418 39

105-107° C. I-1c.406 40

 81-85° C. I-1b.418 41

125-128° C. I-1a.406 42

105-110° C. I-1b.394 43

139-143° C. I-1c.435 44

172-177° C. I-1c.435a 45

138-144° C. I-1a.435 46

208-210° C. I-1a.435a 47

235-236° C. I-1a.457 48

CDCl₃, TMS: 1.55(d, 6H), 2.82(s, 3H), 4.61(m, 1H), 7.39(s, 1H), 7.56(d, 1H), 7.77(d, 1H) ppm. I-1c.397 49

CDCl₃, TMS: 1.08(m, 2H), 1.22(m, 2H), 2.90(s, 3H), 3.40(m, 1H), 7.38(s, 1H), 7.56(d, 1H), 7.90(d, 1H), 8.95(OH), 9.03(s, 1H) ppm. I-1w.394 50

 69-71° C. I-1a.808 51

115-118° C. I-1c.808 52

141-144° C. I-1a.667

The compounds of the formula I and their agriculturally useful salts are suitable, both as isomer mixtures and in the form of the pure isomers, for use as herbicides. The herbicidal compositions comprising compounds of the formula I effect very good control of vegetation on non-crop areas, especially at high application rates. In crops such as wheat, rice, maize, soybeans and cotton, they act against broad-leaved weeds and grass weeds without causing any significant damage to the crop plants. This effect is observed in particular at low application rates.

Depending on the application method in question, the compounds of the formula I or the herbicidal compositions comprising them can additionally be employed in a further number of crop plants for eliminating undesirable plants. Suitable crops are, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea-canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, vitis vinifera and Zea mays.

In addition, the compounds of the formula I can also be used in crops which tolerate the action of herbicides due to breeding, including genetic engineering methods.

The compounds of the formula I, or the compositions comprising them, can be applied, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or pouring. The use forms depend on the intended purposes; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and usually the auxiliaries which are customarily used for formulating crop protection agents.

Suitable inert auxiliaries are essentially: Mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of the formula I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates from active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, and these concentrates are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, of alkyl- and alkylarylsulfonates, of alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and the salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or concomitant grinding of the active substances with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use products can be varied within wide ranges. In general, the formulations comprise approximately from 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The formulation examples which follow illustrate the preparation of such products:

I. 20 parts by weight of the compound of the formula I in question are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

II. 20 parts by weight of the compound of the formula I in question are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III. 20 parts by weight of the compound of the formula I in question are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the compound of the formula I in question are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

V. 3 parts by weight of the compound of the formula I in question are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the compound of the formula I in question are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglylcol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound of the formula I in question is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound of the formula I in question is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol^(R) EM 31 (=non-ionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I, or the herbicidal compositions, can be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, it is possible to use application techniques in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into as little contact as possible, if any, with the leaves of the sensitive crop plants while the active ingredients reach the leaves of undesirable plants which grow underneath, or the bare soil surface (post-directed, lay-by).

Depending on the intended aim, the season, the target plants and the growth stage, the rates of application of the compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active substance (a.s.)/ha.

To widen the spectrum of action and to achieve synergistic effects, the compounds of the formula I according to the invention may be mixed, and applied jointly, with a large number of representatives of other groups of herbicidally or growth-regulating active ingredients. Suitable examples of components in mixtures are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/hetaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, cyclohexanone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds of the formula I, alone or in combination with other herbicides, even in the form of a mixture together with further crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the compounds of the formula I according to the invention was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with translucent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. To this end, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The rate of application for the post-emergence treatment was 0.5 or 0.25 kg of a.s. (active. substance)/ha.

Depending on the species, the plants were kept at from 10 to 25° C., or 20-35° C., respectively. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the following species:

Bayer-code Common name AMARE redroot pigweed AVEFA wild oats CHEAL lambsquarters (goosefoot) CAPBP shepherd's purse DIGSA fingergrass, hairy ECHCG barnyard grass EPHHL spurge GASPA smallflower GALAP catchweed bedstraw LAMAM henbit MYOAR forget-me-not PAPRH corn poppy POLPE ladysthumb SETIT foxtail STEME common chickweed SOLNI black nightshade THLAR fanweed TRZAS spring wheat

At application rates of 0.5 and 0.25 kg/ha (a.s.), the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 1) showed very good herbicidal action against the harmful plants AVEFA, CHEAL, POLPE, SOLNI and GALAP, when applied by the post-emergence method.

At application rates of 0.125 and 0.0625 kg/ha, the compound 4-(2′,4′-dimethylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 14) shows very good herbicidal action against GASPA, LAMAM, STEME, THLAR, when applied by the post-emergence method.

At application rates of 0.125 and 0.0625 kg/ha, the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-benzyloxy-1-methylpyrazole (Example 13) shows very good herbicidal action against CHEAL, EPHHL, MYOAR, PAPRH, SOLNI, and selectivity in wheat when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(2′-ethyl-4′-methylbenzoxazol-5′-ylcarbonyl)-5-hydroxy-1-isopropylpyrazole (Example 31) shows very good herbicidal action against AMARE, CHEAL, LAMAM, PAPRH, POLPE, THLAR, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(2′,4′-dimethylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-isopropylpyrazole (Example 33) shows very good herbicidal action against AMARE, CHEAL, LAMAM, MYOAR, PAPRH, THLAR, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(2′-methoxymethyl-4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 34) shows very good herbicidal action against CHEAL, LAMAM, PAPRH, STEME, THLAR, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(2′-ethyl-4′-methylbenzoxazol-5′-ylcarbonyl)-5-hydroxy-1-methylpyrazole (Example 30) shows very good herbicidal action against CHEAL, LAMAM, PAPRH, POLPE, THLAR, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(2′-methoxymethyl-4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-isopropylpyrazole (Example 36) show very good herbicidal action against CHEAL, EPHHL, MYOAR, PAPRH, SOLNI, STEME, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-hydroxy-1-isopropylpyrazole (Example 12) shows very good herbicidal action against CHEAL, LAMAM, PAPRH, STEME, THLAR, when applied by the post-emergence method.

At application rates of 0.5 and 0.25 kg/ha, the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-(3″-fluorobenzoyl)oxy-1-methylpyrazole (Example 16) shows very good herbicidal action against AMARE, ECHCG, CHEAL, GALAP, POLPE, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-benzoyloxy-1-methylpyrazole (Example 15) shows very good herbicidal action against AVEFA, AMARE, ECHCG, CHEAL, POLPE, when applied by the post-emergence method.

At application rates of 0.25 and 0.125 kg/ha, the compound 4-(4′-methylbenzothiazol-5′-ylcarbonyl)-5-cyclopropylcarbonyloxy-1-methylpyrazole (Example 18) shows very good herbicidal action against AVEFA, AMARE, ECHCG, CHEAL, POLPE, when applied by the post-emergence method. 

We claim:
 1. A pyrazolyl derivative of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formula I,

where X is N or a group C—R³; Y is O, S, SO, SO₂ or NR⁴ or X—Y is S═N, and X is sulfur; R¹ is hydrogen, nitro, halo, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, or di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl; R² is hydrogen, halogen or C₁-C₆-alkyl; R³ is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto, thiocyanato, hydrazide, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-aminoalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-hydroxyalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, is C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of C₁-C₄-alkoxy and hydroxyl, is C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-hydroxyalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl, is phenyl, naphthyl, heterocyclyl, phenylamino, phenoxy, diphenylamino, where the phenyl and heterocyclyl groups of the six last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, is C(O)OR⁵, or C(O)N(R⁶)R¹; and R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, is phenyl, naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; where R⁵ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, is phenyl, naphthyl or heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, are phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and Pz is a radical of the formula IIa or IIb,

 where the variables R⁸, R⁹ and R¹⁰ are as defined below: R⁸ is hydroxyl, mercapto, halogen, OR¹¹, SR¹¹, SOR¹², SO₂R¹², OSO₂R¹², P(O)R¹³R¹⁴, OP(O)R¹³R¹⁴, P(S)R¹³R¹⁴, OP(S)R¹³R¹⁴, NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R⁹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹⁰ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio; where R¹¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, di(C₁-C₆-alkyl)aminothiocarbonyl or C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)—N—(phenyl)aminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)—N—(heterocyclyl)aminocarbonyl, or heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹² is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl; is phenyl, phenyl-C₁-C₆-alkyl, heterocyclyl or heterocyclyl-C₁-C₆-alkyl, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹³ R¹⁴ independently of one another are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹⁵ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following radicals: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆cycloalkyl; is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; and R¹⁶ is hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, C₃-C₆-alkynyl; and its agriculturally useful salts.
 2. A pyrazole derivative as claimed in claim 1 where X in the formula I is C—R³, where R³ is hydrogen, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, is phenyl, phenoxy or pyridyl, where the three last-mentioned radicals may be partially or fully halogenated and/or may carry one of the following radicals: C₁-C₄-alkoxy, C₁-C₄-haloalkyl, and C₁-C₄-haloalkoxy; or is COOR⁵ where R⁵ is as defined in claim
 1. 3. A pyrazole derivative as claimed in claim 1 where X in the formula I is C—R³ and Y is selected from the group consisting of S, SO and SO₂.
 4. A pyrazole derivative as claimed in claim 1, where Y in the formula I is N—R⁴, where R⁴ is as defined in claim 1, and X is C—R³, where R³ is as defined in claim
 1. 5. A pyrazole derivative as claimed in claim 1 where X is N and Y is selected from the group consisting of S, SO, SO₂ and N—R⁴.
 6. A pyrazole derivative as claimed in claim 1 where Pz in the formula I is a radical of the formula IIa, where R⁸ is selected from the group consisting of hydroxyl, OR¹¹ and OSO₂R¹², where R¹¹ and R¹² are as defined in claim 1, R⁹ and R¹⁰ being as defined in claim
 1. 7. A pyrazole derivative as claimed in claim 6, where in the formula IIa R⁸ is hydroxyl, C₁-C₄-alkyloxy, O—CH₂-phenyl, phenylcarbonyloxy, 2-, 3- or 4-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, C₁-C₄-sulfonyloxy, phenylsulfonyloxy and 2-, 3- or 4-methylphenylsulfonyloxy; R⁹ is C₁-C₄-alkyl or cyclopropyl and R¹⁰ is hydrogen or C₁-C₄-alkyl.
 8. A process for preparing compounds of the formula I where R⁸=hydroxyl, as claimed in claim 1, which comprises acylating a 5-hydroxypyrazole of the formula III,

where the variables R⁹ and R¹⁰ are as defined in claim 1 with an activated carboxylic acid IVa or a carboxylic acid IVb

where the variables X, Y, R¹ and R² are as defined in claim 1 and L¹ is nucleophilically replaceable leaving group, and rearranging the acylation product, if appropriate in the presence of a catalyst, to give the compounds I where R⁸=hydroxyl.
 9. A process for preparing compounds of the formula I as claimed in claim 1 where R⁸=halogen, which comprises reacting a pyrazole derivative of the formula I where R⁸=hydroxyl with a halogenating agent.
 10. A process for preparing compounds of the formula I as claimed in claim 1 where R⁸=OR¹¹, OSO₂R¹², OP(O)R¹³R¹⁴ or OP(S)R¹³R¹⁴, which comprises reacting a pyrazole derivative of the formula I where R⁸=hydroxyl with an alkylating agent Vα, sulfonylating agent Vβ or phosphonylating agent Vγ or Vδ, L²-R¹¹ L²-SO₂R¹² L²-P(O)R¹³R¹⁴ L²-P(S)R¹³R¹⁴ IVα IVβ IVγ IVδ

where the variables R¹¹ to R¹⁴ are as defined in claim 1 and L² is a nucleophilically replaceable leaving group.
 11. A process for preparing compounds of the formula I as claimed in claim 1 where R⁸=OR¹¹, SR¹¹, P(O)R¹³R¹⁴, NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl, which comprises reacting a pyrazole derivative of the formula I where R⁸=halogen or OSO₂R¹² with a compound of the formula VIα, VIβ, VIγ, VIδ, VIε or VIη HOR¹¹ HSR¹¹ HPOR¹³R¹⁴ HNR¹⁵R¹⁶ HONR¹⁵R¹⁶ VIα VIβ VIγ VIδ VIε

if appropriate in the presence of a base.
 12. A process for preparing compounds of the formula I where P_(z)=IIa as claimed in claim 1, which comprises reacting a metallated pyrazole derivative of the formula VII, where M is a metal and R⁸ to R¹⁰ are as defined in claim 1 with a carboxylic acid derivative of the formula IVa, where R¹, R², X and Y are as defined in claim 1 and L¹ is a nucleophilically replaceable leaving group.


13. A herbicidal composition, comprising a herbicidally effective amount of at least one pyrazole derivative of the formula I or an agriculturally useful salt of I as defined in claim 1, and customary auxiliaries.
 14. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one pyrazole derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 to act on plants, their habitat and/or on seed.
 15. A pyrazolyl derivative of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formula I,

where X is a group C—R³; Y is O; R¹ is hydrogen, nitro, halo, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, or di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl; R² is hydrogen, halogen or C₁-C₆-alkyl; R³ is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto, thiocyanato, hydrazide, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-aminoalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-hydroxyalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, or is C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of C₁-C₄-alkoxy and hydroxyl, or is C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-hydroxyalkylthio, C₁-C₆-alkoxy-C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl, or is phenyl, naphthyl, phenylamino, phenoxy, diphenylamino, where the phenyl groups of the five last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or is C(O)OR⁵, or C(O)N(R⁶)R⁷; and R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, or is phenyl, naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R⁵ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, or is phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, or are phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and Pz is a radical of the formula IIa or IIb,

 where the variables R⁸, R⁹ and R¹⁰ are as defined below: R⁸ is hydroxyl, mercapto, halogen, OR¹¹, SR¹¹, SOR¹², SO₂R¹², OSO₂R¹², P(O)R¹³R¹⁴, OP(O)R¹³R¹⁴, P(S)R¹³R¹⁴, OP(S)R¹³R¹⁴, NR¹⁵R¹⁶, ONR¹⁵R¹⁶ or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R⁹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹⁰ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio; R¹¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₃-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, di(C₁-C₆-alkyl)aminothiocarbonyl or C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; or is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)—N—(phenyl)aminocarbonyl, or phenyl-C₂-C₆-alkenylcarbonyl, where the phenyl radical of the 9 last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹² is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl; or is phenyl or phenyl-C₁-C₆-alkyl, where the phenyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹³, R¹⁴ independently of one another are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹⁵ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following radicals: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl; or is phenyl, phenyl-C₁-C₄-alkyl or phenylcarbonyl, where the phenyl radical of the three last-mentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; and R¹⁶ is hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, C₃-C₆-alkynyl; and its agriculturally useful salts.
 16. A pyrazole derivative as claimed in claim 15 where R³ is hydrogen, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, or is phenyl, phenoxy or pyridyl, where the three last-mentioned radicals may be partially or fully halogenated and/or may carry one of the following radicals: C₁-C₄-alkoxy, C₁-C₄-haloalkyl, and C₁-C₄-haloalkoxy; or is COOR⁵ where R⁵ is as defined in claim
 15. 